Keywords
amination
aryl and heteroaryl halides
aryl boronic acids
catalysis
immobilized catalysts
Pd and Cu complexes
Abstract
The review deals with the main catalytic methods for the C(sp$^{2}$)--N bond formation, including Buchwald--Hartwig palladium-catalyzed amination of aryl and heteroaryl halides, renaissance of the Ullmann chemistry, \emph{i.e}., the application of catalysis by copper complexes to form the carbon--nitrogen bond, and Chan--Lam reactions of (hetero)arylboronic acids with amines. Also, oxidative amination with C--H activation, which has been booming during the last decade, is addressed. Particular attention is paid to achievements in the application of heterogenized catalysts.
The bibliography includes 350 references.
Funders
Russian Foundation for Basic Research
19-13-50173
References
1.
Ruiz-Castillo P., Buchwald S.L.
Chemical Reviews ,
2016
2.
Heravi M.M., Kheilkordi Z., Zadsirjan V., Heydari M., Malmir M.
Journal of Organometallic Chemistry ,
2018
3.
Dorel R., Grugel C.P., Haydl A.M.
Angewandte Chemie - International Edition ,
2019
4.
Forero-Cortés P.A., Haydl A.M.
Organic Process Research and Development ,
2019
5.
Kosugi M., Kameyama M., Migita T.
Chemistry Letters ,
1983
6.
Dale Boger L., Panek J.S.
Tetrahedron Letters ,
1984
7.
Paul F., Patt J., Hartwig J.F.
Journal of the American Chemical Society ,
1994
8.
Guram A.S., Buchwald S.L.
Journal of the American Chemical Society ,
1994
9.
Guram A.S., Rennels R.A., Buchwald S.L.
1995
10.
Louie J., Hartwig J.F.
Tetrahedron Letters ,
1995
11.
Davydov D.V., Beletskaya I.P.
Russian Chemical Bulletin ,
1995
12.
Beletskaya I.P., Davydov D.V., Moreno-Mañas M.
Tetrahedron Letters ,
1998
13.
Yang B.H., Buchwald S.L.
Journal of Organometallic Chemistry ,
1999
14.
Wolfe J.P., Wagaw S., Buchwald S.L.
Journal of the American Chemical Society ,
1996
15.
Driver M.S., Hartwig J.F.
Journal of the American Chemical Society ,
1996
16.
Hamann B.C., Hartwig J.F.
Journal of the American Chemical Society ,
1998
17.
Guari Y., van Es D.S., Reek J.N., Kamer P.C., van Leeuwen P.W.
Tetrahedron Letters ,
1999
18.
Yin J., Buchwald S.L.
Journal of the American Chemical Society ,
2002
19.
Steinhuebel D., Palucki M., Askin D., Dolling U.
Tetrahedron Letters ,
2004
20.
Artamkina G.A., Sergeev A.G., Beletskaya I.P.
Tetrahedron Letters ,
2001
21.
Hanley P.S., Clark T.P., Krasovskiy A.L., Ober M.S., O’Brien J.P., Staton T.S.
ACS Catalysis ,
2016
22.
Becica J., Dobereiner G.E.
ACS Catalysis ,
2017
23.
Mao J., Zhang J., Zhang S., Walsh P.J.
Dalton Transactions ,
2018
24.
Wolfe J.P., Tomori H., Sadighi J.P., Yin J., Buchwald S.L.
Journal of Organic Chemistry ,
2000
25.
Ingoglia B.T., Wagen C.C., Buchwald S.L.
Tetrahedron ,
2019
26.
Huang X., Anderson K.W., Zim D., Jiang L., Klapars A., Buchwald S.L.
Journal of the American Chemical Society ,
2003
27.
Anderson K.W., Tundel R.E., Ikawa T., Altman R.A., Buchwald S.L.
Angewandte Chemie - International Edition ,
2006
28.
Surry D.S., Buchwald S.L.
Journal of the American Chemical Society ,
2007
29.
Fors B.P., Watson D.A., Biscoe M.R., Buchwald S.L.
Journal of the American Chemical Society ,
2008
30.
Fors B.P., Dooleweerdt K., Zeng Q., Buchwald S.L.
Tetrahedron ,
2009
31.
Maiti D., Fors B.P., Henderson J.L., Nakamura Y., Buchwald S.L.
Chemical Science ,
2011
32.
Ruiz-Castillo P., Blackmond D.G., Buchwald S.L.
Journal of the American Chemical Society ,
2015
33.
Lai W.I., Leung M.P., Choy P.Y., Kwong F.Y.
Synthesis ,
2019
34.
Liu M., Mei Q., Zhang Y., Bai P., Guo X.
Chinese Chemical Letters ,
2017
35.
Pauton M., Gillet R., Aubert C., Bluet G., Gruss-Leleu F., Roy S., Perrio C.
Organic and Biomolecular Chemistry ,
2019
36.
Smith S.M., Buchwald S.L.
Organic Letters ,
2016
37.
McCann S.D., Reichert E.C., Arrechea P.L., Buchwald S.L.
Journal of the American Chemical Society ,
2020
38.
Littke A.F., Fu G.C.
Journal of the American Chemical Society ,
2001
39.
Hartwig J.F., Kawatsura M., Hauck S.I., Shaughnessy K.H., Alcazar-Roman L.M.
Journal of Organic Chemistry ,
1999
40.
Stambuli J.P., Kuwano R., Hartwig J.F.
Angewandte Chemie - International Edition ,
2002
41.
Hartwig J.F.
Accounts of Chemical Research ,
2008
42.
Vo G.D., Hartwig J.F.
Journal of the American Chemical Society ,
2009
43.
Green R.A., Hartwig J.F.
Organic Letters ,
2014
44.
Lundgren R., Peters B., Alsabeh P., Stradiotto M.
Angewandte Chemie - International Edition ,
2010
45.
Lundgren R.J., Stradiotto M.
Angewandte Chemie - International Edition ,
2010
46.
Crawford S.M., Lavery C.B., Stradiotto M.
Chemistry - A European Journal ,
2013
47.
DeAngelis A., Wang D., Buchwald S.L.
Angewandte Chemie - International Edition ,
2013
48.
Schlummer B., Scholz U.
Advanced Synthesis and Catalysis ,
2004
49.
Wang J.Y., Choi K., Zuend S.J., Borate K., Shinde H., Goetz R., Hartwig J.F.
Angewandte Chemie - International Edition ,
2020
50.
Chen Z., Chen X., So C.M.
Journal of Organic Chemistry ,
2019
51.
Tappen J., Rodstein I., McGuire K., Großjohann A., Löffler J., Scherpf T., Gessner V.H.
Chemistry - A European Journal ,
2020
52.
rcr_90_11_1359_bib52
Beletskaya
1998
53.
rcr_90_11_1359_bib53
Zhang
Chem. Sci. ,
2019
54.
Aubin Y., Fischmeister C., Thomas C.M., Renaud J.
Chemical Society Reviews ,
2010
55.
Mann G., Hartwig J.F., Driver M.S., Fernández-Rivas C.
Journal of the American Chemical Society ,
1998
56.
rcr_90_11_1359_bib56
Shen
J. Am. Chem. Soc. ,
2006
57.
Dumrath A., Lübbe C., Neumann H., Jackstell R., Beller M.
Chemistry - A European Journal ,
2011
58.
Alsabeh P.G., Lundgren R.J., McDonald R., Johansson Seechurn C.C., Colacot T.J., Stradiotto M.
Chemistry - A European Journal ,
2013
59.
Naghipour A., Ghorbani-Choghamarani A., Babaee H., Hashemi M., Notash B.
Journal of Organometallic Chemistry ,
2017
60.
Strotman N.A., Soumeillant M.C., Zhu K., Markwalter C.E., Wei C.S., Hsiao Y., Eastgate M.D.
Journal of Organic Chemistry ,
2018
61.
Song H., Yoon E., Heo J.
Tetrahedron Letters ,
2020
62.
rcr_90_11_1359_bib62
Copin
2016
63.
Noël T., Naber J.R., Hartman R.L., McMullen J.P., Jensen K.F., Buchwald S.L.
Chemical Science ,
2011
64.
Chen M., Buchwald S.L.
Angewandte Chemie - International Edition ,
2013
65.
Hartwig J., Ceylan S., Kupracz L., Coutable L., Kirschning A.
Angewandte Chemie - International Edition ,
2013
66.
Baumgartner L.M., Dennis J.M., White N.A., Buchwald S.L., Jensen K.F.
Organic Process Research and Development ,
2019
67.
68.
Louie J., Driver M.S., Hamann B.C., Hartwig J.F.
Journal of Organic Chemistry ,
1997
69.
Taeufer T., Pospech J.
Journal of Organic Chemistry ,
2020
70.
rcr_90_11_1359_bib70
Beletskaya
2005
71.
rcr_90_11_1359_bib71
Averin
2010
72.
Beletskaya I.P., Averin A.D., Bessmertnykh A.G., Denat F., Guilard R.
Russian Journal of Organic Chemistry ,
2010
73.
rcr_90_11_1359_bib73
Averin
2010
74.
rcr_90_11_1359_bib74
Averin
2011
75.
Averin A.D., Beletskaya I.P.
Pure and Applied Chemistry ,
2019
76.
Yakushev A.A., Averin A.D., Maloshitskaya O.A., Koifman O.I., Syrbu S.A., Beletskaya I.P.
Macroheterocycles ,
2018
77.
Yakushev A.A., Averin A.D., Sakovich M.V., Vatsouro I.M., Kovalev V.V., Syrbu S.A., Koifman O.I., Beletskaya I.P.
Journal of Porphyrins and Phthalocyanines ,
2019
78.
Ranyuk E.R., Averin A.D., Beletskaya I.P.
Advanced Synthesis and Catalysis ,
2010
79.
Grigorova O.K., Averin A.D., Maloshitskaya O.A., Rybakov V.B., Beletskaya I.P.
Macroheterocycles ,
2016
80.
Chernichenko N., Shevchuk V., Averin A., Maloshitskaya O., Beletskaya I.
Synlett ,
2017
81.
Chernichenko N.M., Averin A.D., Beletskaya I.P.
Letters in Organic Chemistry ,
2018
82.
Averin A.D., Chernichenko N.M., Shevchuk V.N., Maloshitskaya O.A., Denat F., Beletskaya I.P.
Macroheterocycles ,
2018
83.
Abel A.S., Mitrofanov A.Y., Rousselin Y., Denat F., Bessmertnykh-Lemeune A., Averin A.D., Beletskaya I.P.
ChemPlusChem ,
2015
84.
Abel A.S., Averin A.D., Beletskaya I.P.
New Journal of Chemistry ,
2016
85.
Abel A.S., Averin A.D., Cheprakov A.V., Roznyatovsky V.A., Denat F., Bessmertnykh-Lemeune A., Beletskaya I.P.
Organic and Biomolecular Chemistry ,
2019
86.
Abel A.S., Zenkov I.S., Averin A.D., Cheprakov A.V., Bessmertnykh‐Lemeune A.G., Orlinson B.S., Beletskaya I.P.
ChemPlusChem ,
2019
87.
Grigorova O.K., Averin A.D., Maloshitskaya O.A., Beletskaya I.P.
Macroheterocycles ,
2016
88.
Grigorova O.K., Averin A.D., Maloshitskaya O.A., Beletskaya I.P.
Macroheterocycles ,
2017
89.
Grigorova O.K., Gusev D.I., Averin A.D., Maloshitskaya O.A., Beletskaya I.P.
Russian Chemical Bulletin ,
2019
90.
Grigorova O.K., Averin A.D., Maloshitskaya O.A., Denat F., Beletskaya I.P.
Macroheterocycles ,
2019
91.
Averin A.D., Grigorova O.K., Malysheva A.S., Shaferov A.V., Beletskaya I.P.
Pure and Applied Chemistry ,
2020
92.
Brütting C., Schmidt A., Kataeva O., Knölker H.
Synthesis ,
2018
93.
Spindler B., Kataeva O., Knölker H.
Journal of Organic Chemistry ,
2018
94.
Abengózar A., García-García P., Sucunza D., Pérez-Redondo A., Vaquero J.J.
Chemical Communications ,
2018
95.
Liu Y., Hou H., Zhou Y., Zhao X., Tang C., Tan Y., Müllen K.
Nature Communications ,
2018
96.
Kurata R., Sakamaki D., Uebe M., Kinoshita M., Iwanaga T., Matsumoto T., Ito A.
Organic Letters ,
2017
97.
rcr_90_11_1359_bib97
Cleveland
2017
98.
Pereira A.M., Lacerda P.S., Silva B.N., Neves M.G., Silva A.M., Silva B.V., da Silva F.C., Ferreira V.F., Pinto A.C., Cavaleiro J.A.
Dyes and Pigments ,
2017
99.
Qu Y., Pander P., Vybornyi O., Vasylieva M., Guillot R., Miomandre F., Dias F.B., Skabara P., Data P., Clavier G., Audebert P.
Journal of Organic Chemistry ,
2020
100.
Froese R.D., Lombardi C., Pompeo M., Rucker R.P., Organ M.G.
Accounts of Chemical Research ,
2017
101.
Bastug G., Nolan S.P.
Organometallics ,
2014
102.
Viciu M.S., Kelly R.A., Stevens E.D., Naud F., Studer M., Nolan S.P.
Organic Letters ,
2003
103.
Organ M., Abdel-Hadi M., Avola S., Dubovyk I., Hadei N., Kantchev E., O'Brien C., Sayah M., Valente C.
Chemistry - A European Journal ,
2008
104.
Meiries S., Chartoire A., Slawin A.M., Nolan S.P.
Organometallics ,
2012
105.
Balogh J., Hlil A.R., El-Zoghbi I., Rafique M.G., Chouikhi D., Al-Hashimi M., Bazzi H.S.
Macromolecular Rapid Communications ,
2017
106.
Cao Q., Nicholson W.I., Jones A.C., Browne D.L.
Organic and Biomolecular Chemistry ,
2019
107.
Yoshida Y., Otsuka S., Nogi K., Yorimitsu H.
Organic Letters ,
2018
108.
Al-Taweel S.A., Al-Trawneh S.A., Al-Trawneh W.M.
Cogent Chemistry ,
2019
109.
Nandi D., Islam R.U., Devi N., Siwal S., Mallick K.
New Journal of Chemistry ,
2018
110.
Ganesh Babu S., Emayavaramban B., Jerome P., Karvembu R.
Catalysis Letters ,
2017
111.
Ernst J.B., Schwermann C., Yokota G., Tada M., Muratsugu S., Doltsinis N.L., Glorius F.
Journal of the American Chemical Society ,
2017
112.
Veisi H., Safarimehr P., Hemmati S.
Materials Science and Engineering C ,
2019
113.
Rafiee E., Ataei A., Joshaghani M.
Tetrahedron Letters ,
2016
114.
Al-Amin M., Honma T., Hoshiya N., Shuto S., Arisawa M.
Advanced Synthesis and Catalysis ,
2012
115.
Ullmann F.
European Journal of Inorganic Chemistry ,
1903
116.
Ullmann F.
Berichte der deutschen chemischen Gesellschaft ,
1904
117.
Goldberg I.
European Journal of Inorganic Chemistry ,
1906
118.
Vaidya G.N., Khan A., Verma H., Kumar S., Kumar D.
Journal of Organic Chemistry ,
2019
119.
Ma D., Cai Q.
Accounts of Chemical Research ,
2008
120.
Monnier F., Taillefer M.
Angewandte Chemie - International Edition ,
2009
121.
D. Senra J., C.S. Aguiar L., B.C. Simas A.
Current Organic Synthesis ,
2011
122.
Sambiagio C., Marsden S.P., Blacker A.J., McGowan P.C.
Chemical Society Reviews ,
2014
123.
Evano G., Blanchard N., Toumi M.
Chemical Reviews ,
2008
124.
Okano K., Tokuyama H., Fukuyama T.
Chemical Communications ,
2014
125.
rcr_90_11_1359_bib125
Lee
2013
126.
rcr_90_11_1359_bib126
Junge
2017
127.
rcr_90_11_1359_bib127
Shaughnessy
2017
128.
Neetha M., Saranya S., Ann Harry N., Anilkumar G.
ChemistrySelect ,
2020
129.
Morarji D.V., Gurjar K.K.
Organometallics ,
2019
130.
Monnier F., Taillefer M.
Angewandte Chemie - International Edition ,
2008
131.
Wang D., Cai Q., Ding K.
Advanced Synthesis and Catalysis ,
2009
132.
Zhu Y., Wei Y.
Canadian Journal of Chemistry ,
2011
133.
Jung H.S., Yun T., Cho Y., Jeon H.B.
Tetrahedron ,
2016
134.
Anderson C.A., Taylor P.G., Zeller M.A., Zimmerman S.C.
Journal of Organic Chemistry ,
2010
135.
Ji P., Atherton J.H., Page M.I.
Journal of Organic Chemistry ,
2012
136.
Lang F., Zewge D., Houpis I.N., Volante R.P.
Tetrahedron Letters ,
2001
137.
rcr_90_11_1359_bib137
Xua
2009
138.
Xia N., Taillefer M.
Angewandte Chemie - International Edition ,
2009
139.
Fantasia S., Windisch J., Scalone M.
Advanced Synthesis and Catalysis ,
2013
140.
Fan M., Zhou W., Jiang Y., Ma D.
Organic Letters ,
2015
141.
rcr_90_11_1359_bib141
Zhou
J. Am. Chem. Soc. ,
2015
142.
Gao J., Bhunia S., Wang K., Gan L., Xia S., Ma D.
Organic Letters ,
2017
143.
Zhu D., Wang R., Mao J., Xu L., Wu F., Wan B.
Journal of Molecular Catalysis A Chemical ,
2006
144.
Kelkar A.A., Patil N.M., Chaudhari R.V.
Tetrahedron Letters ,
2002
145.
Cu(II)-Catalyzed C-N Coupling of (Hetero)aryl Halides and N-Nucleophiles Promoted by α-Benzoin Oxime
Yuan C., Zhang L., Zhao Y.
Molecules ,
2019
146.
Sharghi H., Sepehri S., Aberi M.
Molecular Diversity ,
2017
147.
rcr_90_11_1359_bib147
Banerjee
J. Org. Chem. ,
2016
148.
Kwong F.Y., Klapars A., Buchwald S.L.
Organic Letters ,
2002
149.
Zhang H., Cai Q., Ma D.
Journal of Organic Chemistry ,
2005
150.
rcr_90_11_1359_bib150
Wang
2009
151.
Yang C., Fu Y., Huang Y., Yi J., Guo Q., Liu L.
Angewandte Chemie - International Edition ,
2009
152.
Deldaele C., Evano G.
ChemCatChem ,
2016
153.
Yang K., Qiu Y., Li Z., Wang Z., Jiang S.
Journal of Organic Chemistry ,
2011
154.
Zhang Y., Yang X., Yao Q., Ma D.
Organic Letters ,
2012
155.
Lu Z., Twieg R.J.
Tetrahedron ,
2005
156.
Guo X., Rao H., Fu H., Jiang Y., Zhao Y.
Advanced Synthesis and Catalysis ,
2006
157.
Altman R.A., Anderson K.W., Buchwald S.L.
Journal of Organic Chemistry ,
2008
158.
rcr_90_11_1359_bib158
Yang
2011
159.
Mboyi C.D., Vivier D., Daher A., Fleurat‐Lessard P., Cattey H., Devillers C.H., Bernhard C., Denat F., Roger J., Hierso J.
Angewandte Chemie - International Edition ,
2019
160.
Bollenbach M., Wagner P., Aquino P.G., Bourguignon J., Bihel F., Salomé C., Schmitt M.
ChemSusChem ,
2016
161.
Quivelli A.F., Vitale P., Perna F.M., Capriati V.
Frontiers in Chemistry ,
2019
162.
Panchenko S.P., Abel A.S., Averin A.D., Maloshitskaya O.A., Savelyev E.N., Orlinson B.S., Novakov I.A., Beletskaya I.P.
Russian Journal of Organic Chemistry ,
2017
163.
Averin A.D., Panchenko S.P., Abel A.S., Maloshitskaya O.A., Butov G.M., Savelyev E.N., Orlinson B.S., Novakov I.A., Beletskaya I.P.
Russian Journal of Organic Chemistry ,
2017
164.
Abel A.S., Averin A.D., Anokhin M.V., Maloshitskaya O.A., Butov G.M., Savelyev E.N., Orlinson B.S., Novakov I.A., Beletskaya I.P.
Russian Journal of Organic Chemistry ,
2015
165.
Lyakhovich M.S., Murashkina A.V., Averin A.D., Abel A.S., Maloshitskaya O.A., Savelyev E.N., Orlinson B.S., Beletskaya I.P.
Russian Journal of Organic Chemistry ,
2019
166.
D. Averin A., S. Abel A., N. Kotovshchikov Y., A. Maloshitskaya O., N. Savelyev E., S. Orlinson B., A. Novakov I., P. Beletskaya I.
Heterocycles ,
2019
167.
rcr_90_11_1359_bib167
Anokhin
2011
168.
Panchenko S.P., Averin A.D., Anokhin M.V., Maloshitskaya O.A., Beletskaya I.P.
Beilstein Journal of Organic Chemistry ,
2015
169.
Anokhin M.V., Averin A.D., Panchenko S.P., Maloshitskaya O.A., Buryak A.K., Beletskaya I.P.
Helvetica Chimica Acta ,
2015
170.
Panchenko S.P., Averin A.D., Lyakhovich M.S., Abel A.S., Maloshitskaya O.A., Beletskaya I.P.
Russian Chemical Bulletin ,
2017
171.
Lyakhovich M.S., Averin A.D., Grigorova O.K., Roznyatovsky V.A., Maloshitskaya O.A., Beletskaya I.P.
Molecules ,
2020
172.
Averin A.D., Abel A.S., Grigorova O.K., Latyshev G.V., Kotovshchikov Y.N., Mitrofanov A.Y., Bessmertnykh-Lemeune A., Beletskaya I.P.
Pure and Applied Chemistry ,
2020
173.
Klapars A., Antilla J.C., Huang X., Buchwald S.L.
Journal of the American Chemical Society ,
2001
174.
Cristau H., Cellier P.P., Spindler J., Taillefer M.
Chemistry - A European Journal ,
2004
175.
Deng W., Wang Y., Zou Y., Liu L., Guo Q.
Tetrahedron Letters ,
2004
176.
Lv X., Bao W.
Journal of Organic Chemistry ,
2007
177.
Gurjar K.K., Sharma R.K.
Heliyon ,
2020
178.
Kiyomori A., Marcoux J., Buchwald S.L.
Tetrahedron Letters ,
1999
179.
Altman R.A., Buchwald S.L.
Organic Letters ,
2006
180.
Pawar G.G., Wu H., De S., Ma D.
Advanced Synthesis and Catalysis ,
2017
181.
Li X., Yang D., Jiang Y., Fu H.
Green Chemistry ,
2010
182.
Larsson P., Correa A., Carril M., Norrby P., Bolm C.
Angewandte Chemie - International Edition ,
2009
183.
Larsen A.F., Ulven T.
Chemical Communications ,
2014
184.
Marín M., Rama R.J., Nicasio M.C.
Chemical Record ,
2016
185.
Ritleng V., Henrion M., Chetcuti M.J.
ACS Catalysis ,
2016
186.
Ge S., Green R.A., Hartwig J.F.
Journal of the American Chemical Society ,
2014
187.
Liu R.Y., Dennis J.M., Buchwald S.L.
Journal of the American Chemical Society ,
2020
188.
rcr_90_11_1359_bib188
Inaloo
New J. Chem. ,
2020
189.
Park B.Y., Pirnot M.T., Buchwald S.L.
Journal of Organic Chemistry ,
2020
190.
Kang Q., Lin Y., Li Y., Shi H.
Journal of the American Chemical Society ,
2020
191.
Simons R.T., Scott G.E., Kanegusuku A.G., Roizen J.L.
Journal of Organic Chemistry ,
2020
192.
Rodriguez J., Adet N., Saffon-Merceron N., Bourissou D.
Chemical Communications ,
2020
193.
Ghorai S.K., Gopalsamuthiram V.G., Jawalekar A.M., Patre R.E., Pal S.
Tetrahedron ,
2017
194.
Gawande M.B., Goswami A., Felpin F., Asefa T., Huang X., Silva R., Zou X., Zboril R., Varma R.S.
Chemical Reviews ,
2016
195.
rcr_90_11_1359_bib195
Chouhan
2007
196.
rcr_90_11_1359_bib196
Chen
J. Am. Chem. Soc. ,
2007
197.
rcr_90_11_1359_bib197
Arundhathi
2010
198.
Hemmati S., Ahany Kamangar S., Yousefi M., Hashemi Salehi M., Hekmati M.
Applied Organometallic Chemistry ,
2020
199.
Hosseinzadeh R., Aghili N., Tajbakhsh M.
Catalysis Letters ,
2015
200.
Zahmatkesh S., Esmaeilpour M., Javidi J.
RSC Advances ,
2016
201.
Islam M., Mondal S., Mondal P., Roy A.S., Tuhina K., Mobarok M., Paul S., Salam N., Hossain D.
Catalysis Letters ,
2011
202.
Kantam M.L., Roy M., Roy S., Sreedhar B., Lal De R.
Catalysis Communications ,
2008
203.
Islam S.M., Salam N., Mondal P., Roy A.S., Ghosh K., Tuhina K.
Journal of Molecular Catalysis A Chemical ,
2014
204.
Bukowska A., Bukowski W., Bester K., Hus K.
Applied Organometallic Chemistry ,
2017
205.
Likhar P.R., Roy S., Roy M., Kantam M.L., De R.L.
Journal of Molecular Catalysis A Chemical ,
2007
206.
Niakan M., Asadi Z., Zare S.
ChemistrySelect ,
2020
207.
Veisi H., Hamelian M., Hemmati S., Dalvand A.
Tetrahedron Letters ,
2017
208.
Veisi H., Metghalchi Y., Hekmati M., Samadzadeh S.
Applied Organometallic Chemistry ,
2016
209.
Sardarian A.R., Zohourian-Mashmoul N., Esmaeilpour M.
Monatshefte fur Chemie ,
2018
210.
Sardarian A.R., Eslahi H., Esmaeilpour M.
ChemistrySelect ,
2018
211.
Bagheri S., Pazoki F., Radfar I., Heydari A.
Applied Organometallic Chemistry ,
2020
212.
Hajipour A.R., Check M., Khorsandi Z.
Applied Organometallic Chemistry ,
2017
213.
Esmaeilpour M., Sardarian A.R., Firouzabadi H.
Applied Organometallic Chemistry ,
2018
214.
Mitrofanov A.Y., Murashkina A.V., Martín-García I., Alonso F., Beletskaya I.P.
Catalysis Science and Technology ,
2017
215.
Amal Joseph P.J., Priyadarshini S., Lakshmi Kantam M., Maheswaran H.
Catalysis Science and Technology ,
2011
216.
rcr_90_11_1359_bib216
Islam
RSC Adv. ,
2016
217.
Drabina P., Svoboda J., Sedlák M.
Molecules ,
2017
218.
rcr_90_11_1359_bib218
Liu
New J. Chem. ,
2018
219.
Chan D.M., Monaco K.L., Wang R., Winters M.P.
Tetrahedron Letters ,
1998
220.
Lam P.Y., Clark C.G., Saubern S., Adams J., Winters M.P., Chan D.M., Combs A.
Tetrahedron Letters ,
1998
221.
Chen J., Li J., Dong Z.
Advanced Synthesis and Catalysis ,
2020
222.
rcr_90_11_1359_bib222
Dodonov
Zh. Obshch. Khim. ,
1985
223.
Barton D.H., Finet J., Khamsi J.
Tetrahedron Letters ,
1986
224.
Chan D.M.
Tetrahedron Letters ,
1996
225.
Evans D.A., Katz J.L., West T.R.
Tetrahedron Letters ,
1998
226.
Allen S.E., Walvoord R.R., Padilla-Salinas R., Kozlowski M.C.
Chemical Reviews ,
2013
227.
Munir I., Zahoor A.F., Rasool N., Naqvi S.A., Zia K.M., Ahmad R.
Molecular Diversity ,
2018
228.
West M.J., Fyfe J.W., Vantourout J.C., Watson A.J.
Chemical Reviews ,
2019
229.
King A.E., Ryland B.L., Brunold T.C., Stahl S.S.
Organometallics ,
2012
230.
Vantourout J.C., Miras H.N., Isidro-Llobet A., Sproules S., Watson A.J.
Journal of the American Chemical Society ,
2017
231.
Hardouin Duparc V., Schaper F.
Organometallics ,
2017
232.
Hardouin Duparc V., Bano G.L., Schaper F.
ACS Catalysis ,
2018
233.
Vantourout J.C., Li L., Bendito-Moll E., Chabbra S., Arrington K., Bode B.E., Isidro-Llobet A., Kowalski J.A., Nilson M.G., Wheelhouse K.M., Woodard J.L., Xie S., Leitch D.C., Watson A.J.
ACS Catalysis ,
2018
234.
Vantourout J.C., Law R.P., Isidro-Llobet A., Atkinson S.J., Watson A.J.
Journal of Organic Chemistry ,
2016
235.
Roy S., Sarma M.J., Kashyap B., Phukan P.
Chemical Communications ,
2016
236.
Tzschucke C.C., Murphy J.M., Hartwig J.F.
Organic Letters ,
2007
237.
Cheng H., Song W., Nie R., Wang Y., Li H., Jiang X., Wu J., Chen C., Wu Q.
Bioorganic and Medicinal Chemistry Letters ,
2018
238.
Gomaa M.S., Lim A.S., Wilson Lau S.C., Watts A., Illingworth N.A., Bridgens C.E., Veal G.J., Redfern C.P., Brancale A., Armstrong J.L., Simons C.
Bioorganic and Medicinal Chemistry ,
2012
239.
Imanishi M., Tomishima Y., Itou S., Hamashima H., Nakajima Y., Washizuka K., Sakurai M., Matsui S., Imamura E., Ueshima K., Yamamoto T., Yamamoto N., Ishikawa H., Nakano K., Unami N., et. al.
Journal of Medicinal Chemistry ,
2008
240.
Chen Z., Kim S., Barbosa S.A., Huynh T., Tortolani D.R., Leavitt K.J., Wei D.D., Manne V., Ricca C.S., Gullo-Brown J., Poss M.A., Vaccaro W., Salvati M.E.
Bioorganic and Medicinal Chemistry Letters ,
2006
241.
Vergelli C., Schepetkin I.A., Ciciani G., Cilibrizzi A., Crocetti L., Giovannoni M.P., Guerrini G., Iacovone A., Kirpotina L.N., Khlebnikov A.I., Ye R.D., Quinn M.T.
Bioorganic and Medicinal Chemistry ,
2016
242.
Smith A.L., D’Angelo N.D., Bo Y.Y., Booker S.K., Cee V.J., Herberich B., Hong F., Jackson C.L., Lanman B.A., Liu L., Nishimura N., Pettus L.H., Reed A.B., Tadesse S., Tamayo N.A., et. al.
Journal of Medicinal Chemistry ,
2012
243.
Barlaam B., Cosulich S., Degorce S., Fitzek M., Green S., Hancox U., Lambert-van der Brempt C., Lohmann J., Maudet M., Morgentin R., Pasquet M., Péru A., Plé P., Saleh T., Vautier M., et. al.
Journal of Medicinal Chemistry ,
2015
244.
Judd W.R., Slattum P.M., Hoang K.C., Bhoite L., Valppu L., Alberts G., Brown B., Roth B., Ostanin K., Huang L., Wettstein D., Richards B., Willardsen J.A.
Journal of Medicinal Chemistry ,
2011
245.
Li G., Stamford A.W., Huang Y., Cheng K., Cook J., Farley C., Gao J., Ghibaudi L., Greenlee W.J., Guzzi M., van Heek M., Hwa J.J., Kelly J., Mullins D., Parker E.M., et. al.
Bioorganic and Medicinal Chemistry Letters ,
2008
246.
10.1021/jo020696+
247.
Rossi S.A., Shimkin K.W., Xu Q., Mori-Quiroz L.M., Watson D.A.
Organic Letters ,
2013
248.
Lasalle M., Hoguet V., Hennuyer N., Leroux F., Piveteau C., Belloy L., Lestavel S., Vallez E., Dorchies E., Duplan I., Sevin E., Culot M., Gosselet F., Boulahjar R., Herledan A., et. al.
Journal of Medicinal Chemistry ,
2017
249.
Sahoo H., Mukherjee S., Grandhi G.S., Selvakumar J., Baidya M.
Journal of Organic Chemistry ,
2017
250.
Zhang X., Cai C., Winters M., Wells M., Wall M., Lanter J., Sui Z., Ma J., Novack A., Nashashibi I., Wang Y., Yan W., Suckow A., Hua H., Bell A., et. al.
Bioorganic and Medicinal Chemistry Letters ,
2017
251.
Campbell Brewer A., Hoffman P.C., Martinelli J.R., Kobierski M.E., Mullane N., Robbins D.
Organic Process Research and Development ,
2019
252.
rcr_90_11_1359_bib252
Li
Chem. Commun. ,
2012
253.
Dropinski J.F., Akiyama T., Einstein M., Habulihaz B., Doebber T., Berger J.P., Meinke P.T., Shi G.Q.
Bioorganic and Medicinal Chemistry Letters ,
2005
254.
Singh B.K., Appukkuttan P., Claerhout S., Parmar V.S., Van der Eycken E.
Organic Letters ,
2006
255.
Vilapara K.V., Gami S.P., Gadara S.A., Naliapara Y.T.
Asian Journal of Chemistry ,
2019
256.
Motornov V., Latyshev G.V., Kotovshchikov Y.N., Lukashev N.V., Beletskaya I.P.
Advanced Synthesis and Catalysis ,
2019
257.
Akatyev N., Il'in M., Il'in(Jr.) M., Peregudova S., Peregudov A., Buyanovskaya A., Kudryavtsev K., Dubovik A., Grinberg V., Orlov V., Pavlov A., Novikov V., Volkov I., Belokon Y.
ChemCatChem ,
2020
258.
rcr_90_11_1359_bib258
Cope
2020
259.
Wexler R.P., Nuhant P., Senter T.J., Gale-Day Z.J.
Organic Letters ,
2019
260.
Khan A., Karim R., Dhimane H., Alam S.
ChemistrySelect ,
2019
261.
Guchhait S.K., Saini M.
New Journal of Chemistry ,
2020
262.
Synthesis of 1-Vinyl/Arylbenzotriazole 3-Oxides through a Copper-Mediated C-N Bond Coupling Reaction
Shi W., Liu F., Wang Z., Bi H., Liang C., Xu L., Su G., Mo D.
Advanced Synthesis and Catalysis ,
2017
263.
Chen C., Liu Q., Ma X., Feng Y., Liang C., Pan C., Su G., Mo D.
Journal of Organic Chemistry ,
2017
264.
Gupta S., Baranwal S., Muniyappan N., Sabiah S., Kandasamy J.
Synthesis ,
2019
265.
Zu W., Liu S., Jia X., Xu L.
Organic Chemistry Frontiers ,
2019
266.
Ando S., Hirota Y., Matsunaga H., Ishizuka T.
Tetrahedron Letters ,
2019
267.
Islam S.M., Mondal S., Mondal P., Roy A.S., Tuhina K., Salam N., Mobarak M.
Journal of Organometallic Chemistry ,
2012
268.
Seyedi N., Shahabi Nejad M., Saidi K., Sheibani H.
Applied Organometallic Chemistry ,
2019
269.
Gajare S., Jagadale M., Naikwade A., Bansode P., Rashinkar G.
Applied Organometallic Chemistry ,
2019
270.
A new copper complex on graphene oxide: A heterogeneous catalyst for N ‐arylation and C‐H activation
Mittal A., Kumari S., Parmanand, Yadav D., Sharma S.K.
Applied Organometallic Chemistry ,
2019
271.
Kumar A., Layek S., Agrahari B., Kujur S., Pathak D.D.
ChemistrySelect ,
2019
272.
Thakur A., Borah R., Raul P., Mahanta A., Shchukarev A., Mikkola J.
Synlett ,
2017
273.
Das S.K., Deka P., Chetia M., Deka R.C., Bharali P., Bora U.
Catalysis Letters ,
2017
274.
Khosravi A., Mokhtari J., Naimi-Jamal M.R., Tahmasebi S., Panahi L.
RSC Advances ,
2017
275.
Muñoz A., Leo P., Orcajo G., Martínez F., Calleja G.
ChemCatChem ,
2019
276.
Amadine O., Essamlali Y., Amedlous A., Zahouily M.
RSC Advances ,
2019
277.
Vibhute S.P., Mhaldar P.M., Gaikwad D.S., Shejwal R.V., Pore D.M.
Monatshefte fur Chemie ,
2020
278.
Sarmah M., Dewan A., Boruah P.K., Das M.R., Bora U.
Applied Organometallic Chemistry ,
2020
279.
Jamwal B., Kaur M., Sharma H., Khajuria C., Paul S., Clark J.H.
New Journal of Chemistry ,
2019
280.
Park Y., Kim Y., Chang S.
Chemical Reviews ,
2017
281.
Henry M., Mostafa M., Sutherland A.
Synthesis ,
2017
282.
Kim H., Chang S.
Accounts of Chemical Research ,
2017
283.
Gensch T., Hopkinson M.N., Glorius F., Wencel-Delord J.
Chemical Society Reviews ,
2016
284.
Daugulis O., Roane J., Tran L.D.
Accounts of Chemical Research ,
2015
285.
Wan J., Jing Y.
Beilstein Journal of Organic Chemistry ,
2015
286.
Louillat M., Patureau F.W.
Chemical Society Reviews ,
2014
287.
Collet F., Lescot C., Dauban P.
Chemical Society Reviews ,
2011
288.
Zhang M.
Applied Organometallic Chemistry ,
2010
289.
Lyons T.W., Sanford M.S.
Chemical Reviews ,
2010
290.
rcr_90_11_1359_bib290
Tsang
J. Am. Chem. Soc. ,
2005
291.
Tsang W.C., Munday R.H., Brasche G., Zheng N., Buchwald S.L.
Journal of Organic Chemistry ,
2008
292.
Inamoto K., Saito T., Katsuno M., Sakamoto T., Hiroya K.
Organic Letters ,
2007
293.
Miura T., Ito Y., Murakami M.
Chemistry Letters ,
2009
294.
Xiao Q., Wang W., Liu G., Meng F., Chen J., Yang Z., Shi Z.
Chemistry - A European Journal ,
2009
295.
Kumar R.K., Ali M.A., Punniyamurthy T.
Organic Letters ,
2011
296.
Yang W., Chen J., Huang X., Ding J., Liu M., Wu H.
Organic Letters ,
2014
297.
Clagg K., Hou H., Weinstein A.B., Russell D., Stahl S.S., Koenig S.G.
Organic Letters ,
2016
298.
Nadres E.T., Daugulis O.
Journal of the American Chemical Society ,
2011
299.
He G., Lu C., Zhao Y., Nack W.A., Chen G.
Organic Letters ,
2012
300.
Wang C., Chen C., Zhang J., Han J., Wang Q., Guo K., Liu P., Guan M., Yao Y., Zhao Y.
Angewandte Chemie - International Edition ,
2014
301.
Tran L.D., Roane J., Daugulis O.
Angewandte Chemie - International Edition ,
2013
302.
Roane J., Daugulis O.
Journal of the American Chemical Society ,
2016
303.
Singh B.K., Polley A., Jana R.
Journal of Organic Chemistry ,
2016
304.
Tran N.T., Tran Q.H., Truong T.
Journal of Catalysis ,
2014
305.
CH Functionalization/CN Bond Formation: Copper-Catalyzed Synthesis of Benzimidazoles from Amidines
Brasche G., Buchwald S.
Angewandte Chemie - International Edition ,
2008
306.
Wang X., Jin Y., Zhao Y., Zhu L., Fu H.
Organic Letters ,
2011
307.
Takamatsu K., Hirano K., Satoh T., Miura M.
Organic Letters ,
2014
308.
Takamatsu K., Hirano K., Satoh T., Miura M.
Journal of Organic Chemistry ,
2015
309.
Yan Q., Chen Z., Yu W., Yin H., Liu Z., Zhang Y.
Organic Letters ,
2015
310.
Grandhi G.S., Dana S., Mandal A., Baidya M.
Organic Letters ,
2020
311.
Shang M., Sun S., Dai H., Yu J.
Journal of the American Chemical Society ,
2014
312.
Martínez Á.M., Rodríguez N., Arrayás R.G., Carretero J.C.
Chemical Communications ,
2014
313.
Shang M., Shao Q., Sun S., Chen Y., Xu H., Dai H., Yu J.
Chemical Science ,
2017
314.
Li Q., Zhang S., He G., Ai Z., Nack W.A., Chen G.
Organic Letters ,
2014
315.
Yamamoto C., Takamatsu K., Hirano K., Miura M.
Journal of Organic Chemistry ,
2017
316.
Chen X., Hao X., Goodhue C.E., Yu J.
Journal of the American Chemical Society ,
2006
317.
Uemura T., Imoto S., Chatani N.
Chemistry Letters ,
2006
318.
Shuai Q., Deng G., Chua Z., Bohle D.S., Li C.
Advanced Synthesis and Catalysis ,
2010
319.
rcr_90_11_1359_bib319
Kim
J. Am. Chem. Soc. ,
2018
320.
Xu H., Qiao X., Yang S., Shen Z.
Journal of Organic Chemistry ,
2014
321.
Zhu C., Yi M., Wei D., Chen X., Wu Y., Cui X.
Organic Letters ,
2014
322.
Li G., Jia C., Sun K.
Organic Letters ,
2013
323.
Monguchi D., Fujiwara T., Furukawa H., Mori A.
Organic Letters ,
2009
324.
Wang Q., Schreiber S.L.
Organic Letters ,
2009
325.
Guo S., Qian B., Xie Y., Xia C., Huang H.
Organic Letters ,
2011
326.
Li Y., Xie Y., Zhang R., Jin K., Wang X., Duan C.
Journal of Organic Chemistry ,
2011
327.
Liang T., Zhao H., Gong L., Jiang H., Zhang M.
iScience ,
2019
328.
Zhao H., Wang M., Su W., Hong M.
Advanced Synthesis and Catalysis ,
2010
329.
rcr_90_11_1359_bib329
Kim
J. Am. Chem. Soc. ,
2011
330.
Sun K., Li Y., Zhang Q.
Science China Chemistry ,
2015
331.
Morofuji T., Ikarashi G., Kano N.
Organic Letters ,
2020
332.
Stavropoulos P.
Comments on Inorganic Chemistry ,
2016
333.
Shrestha R., Mukherjee P., Tan Y., Litman Z.C., Hartwig J.F.
Journal of the American Chemical Society ,
2013
334.
Marchetti L., Kantak A., Davis R., DeBoef B.
Organic Letters ,
2014
335.
Sun K., Li Y., Feng R., Mu S., Wang X., Zhang B.
Journal of Organic Chemistry ,
2019
336.
Li X., Zhang C., Wang C., Ye W., Zhang Q., Zhang Z., Su J., Chen Y., Tian H.
Chemical Communications ,
2020
337.
Liu X., Sheng H., Zhou Y., Song Q.
Chemical Communications ,
2020
338.
Wang H., Lu Y., Zhang B., He J., Xu H., Kang Y., Sun W., Yu J.
Angewandte Chemie - International Edition ,
2017
339.
Vu H., Yong J., Chen F., Li X., Shi G.
Journal of Organic Chemistry ,
2020
340.
Dong Y., Sun S., Yu J., Cheng J.
Tetrahedron Letters ,
2019
341.
Kim H., Chang S.
ACS Catalysis ,
2015
342.
Kim H., Shin K., Chang S.
Journal of the American Chemical Society ,
2014
343.
Xiong H., Gu Y., Zhang S., Lu F., Ji Q., Liu L., Ma P., Yang G., Hou W., Xu H.
Chemical Communications ,
2020
344.
Xu H., Yang J., Chai X., Zhu Y., Dong L.
Organic Letters ,
2020
345.
Santoro S., Kozhushkov S.I., Ackermann L., Vaccaro L.
Green Chemistry ,
2016
346.
Truong T., Nguyen K.D., Doan S.H., Phan N.T.
Applied Catalysis A: General ,
2016
347.
Tu T.N., Nguyen K.D., Nguyen T.N., Truong T., Phan N.T.
Catalysis Science and Technology ,
2016
348.
Pal P., Giri A.K., Singh H., Ghosh S.C., Panda A.B.
Chemistry - An Asian Journal ,
2014
349.
rcr_90_11_1359_bib349
Singh
2017
350.
Hickman A.J., Sanford M.S.
Nature ,
2012