Keywords
alkaline earth metals
alkyl complexes
catalytic activity
divalent lanthanides
reactivity
structure
synthesis
Abstract
The review presents data on the synthesis, structure, reactivity, and catalytic activity of alkyl derivatives of rare earth metals in the oxidation state +2 (Sm, Eu, Yb) and their analogues containing heavy alkaline earth metals (Ca, Sr, Ba). The synthetic aspects and structural features of this unique class of organometallic compounds, which contain highly reactive M--C bonds, including alkyl, $\alpha$-silylmethyl, and also benzyl, diphenylmethyl, and triphenylmethyl derivatives are considered.
The bibliography includes 157 references.
Funders
Russian Foundation for Basic Research
19-13-50411
References
1.
rcr_90_5_529bib1
Nicholas
2017
2.
Harder S.
Chemical Reviews ,
2010
3.
Barrett A.G., Crimmin M.R., Hill M.S., Procopiou P.A.
Proceedings of the Royal Society A: Mathematical, Physical and Engineering Sciences ,
2010
4.
Zimmermann M., Anwander R.
Chemical Reviews ,
2010
5.
Marques N., Sella A., Takats J.
Chemical Reviews ,
2002
6.
Cotton S.A.
Coordination Chemistry Reviews ,
1997
7.
Piers W.E., Emslie D.J.
Coordination Chemistry Reviews ,
2002
8.
Trifonov A.A.
Russian Chemical Reviews ,
2007
9.
Trifonov A.A., Lyubov D.M.
Coordination Chemistry Reviews ,
2017
10.
Trifonov A.A.
Coordination Chemistry Reviews ,
2010
11.
Nishiura M., Hou Z.
Nature Chemistry ,
2010
12.
Nishiura M., Guo F., Hou Z.
Accounts of Chemical Research ,
2015
13.
Johnson K.R., Hayes P.G.
Chemical Society Reviews ,
2013
14.
Tsurugi H., Yamamoto K., Nagae H., Kaneko H., Mashima K.
Dalton Transactions ,
2014
15.
Arnold J.S., Mwenda E.T., Nguyen H.M.
Angewandte Chemie - International Edition ,
2014
16.
Guan B., Hou Z.
Journal of the American Chemical Society ,
2011
17.
Guan B., Wang B., Nishiura M., Hou Z.
Angewandte Chemie - International Edition ,
2013
18.
rcr_90_5_529bib18
Song
J. Am. Chem. Soc. ,
2014
19.
Oyamada J., Hou Z.
Angewandte Chemie - International Edition ,
2012
20.
Shi X., Nishiura M., Hou Z.
Journal of the American Chemical Society ,
2016
21.
Nako A.E., Oyamada J., Nishiura M., Hou Z.
Chemical Science ,
2016
22.
Luo Y., Ma Y., Hou Z.
Journal of the American Chemical Society ,
2017
23.
Oyamada J., Nishiura M., Hou Z.
Angewandte Chemie - International Edition ,
2011
24.
Watson P.L.
Journal of the American Chemical Society ,
1983
25.
Watson P.L., Parshall G.W.
Accounts of Chemical Research ,
1985
26.
Sadow A.D., Tilley T.D.
Angewandte Chemie - International Edition ,
2003
27.
28.
Gromada J., Carpentier J., Mortreux A.
Coordination Chemistry Reviews ,
2004
29.
Friebe L., Nuyken O., Obrecht W.
30.
rcr_90_5_529bib30
Baugh
2008
31.
Zimmermann M., Törnroos K., Anwander R.
Angewandte Chemie - International Edition ,
2008
32.
Zhang Z., Cui D., Wang B., Liu B., Yang Y.
Structure and Bonding ,
2010
33.
rcr_90_5_529bib33
Takeuchi
2013
34.
Jeske G., Lauke H., Mauermann H., Swepston P.N., Schumann H., Marks T.J.
Journal of the American Chemical Society ,
1985
35.
Jeske G., Schock L.E., Swepston P.N., Schumann H., Marks T.J.
Journal of the American Chemical Society ,
1985
36.
10.1021/cr010291+
37.
Hong S., Marks T.J.
Accounts of Chemical Research ,
2004
38.
Müller T.E., Hultzsch K.C., Yus M., Foubelo F., Tada M.
Chemical Reviews ,
2008
39.
Hannedouche J., Collin J., Trifonov A., Schulz E.
Journal of Organometallic Chemistry ,
2011
40.
Douglass M.R., Stern C.L., Marks T.J.
Journal of the American Chemical Society ,
2001
41.
Douglass M.R., Marks T.J.
Journal of the American Chemical Society ,
2000
42.
Trifonov A.A., Basalov I.V., Kissel A.A.
Dalton Transactions ,
2016
43.
Weiss C.J., Marks T.J.
Dalton Transactions ,
2010
44.
Weiss C.J., Wobser S.D., Marks T.J.
Journal of the American Chemical Society ,
2009
45.
Weiss C.J., Wobser S.D., Marks T.J.
Organometallics ,
2010
46.
Shannon R.D.
Acta Crystallographica Section A ,
1976
47.
Jia Y.Q.
Journal of Solid State Chemistry ,
1991
48.
Harder S.
Angewandte Chemie - International Edition ,
2004
49.
Westerhausen M., Koch A., Görls H., Krieck S.
Chemistry - A European Journal ,
2016
50.
Heckmann G., Niemeyer M.
Journal of the American Chemical Society ,
2000
51.
Ali S.H., Deacon G.B., Junk P.C., Hamidi S., Wiecko M., Wang J.
Chemistry - A European Journal ,
2017
52.
Koch A., Dufrois Q., Wirgenings M., Görls H., Krieck S., Etienne M., Pohnert G., Westerhausen M.
Chemistry - A European Journal ,
2018
53.
Westerhausen M.
Angewandte Chemie - International Edition ,
2001
54.
rcr_90_5_529bib54
Alexander
2002
55.
Buchanan W.D., Allis D.G., Ruhlandt-Senge K.
Chemical Communications ,
2010
56.
Abakumov G.A., Piskunov A.V., Cherkasov V.K., Fedushkin I.L., Ananikov V.P., Eremin D.B., Gordeev E.G., Beletskaya I.P., Averin A.D., Bochkarev M.N., Trifonov A.A., Dzhemilev U.M., D'yakonov V.A., Egorov M.P., Vereshchagin A.N., et. al.
Russian Chemical Reviews ,
2018
57.
Torvisco A., Ruhlandt-Senge K.
Topics in Organometallic Chemistry ,
2013
58.
Payne D.A., Sanderson R.T.
Journal of the American Chemical Society ,
1958
59.
rcr_90_5_529bib59
Bryce-Smith
1963
60.
rcr_90_5_529bib60
Evans
1971
61.
Wolf B.M., Stuhl C., Maichle-Mössmer C., Anwander R.
Journal of the American Chemical Society ,
2018
62.
rcr_90_5_529bib62
Wilson
2017
63.
rcr_90_5_529bib63
Wilson
Angew. Chem., Int. Ed. ,
2018
64.
Wilson A.S., Hill M.S., Mahon M.F.
Organometallics ,
2018
65.
Rösch B., Gentner T.X., Elsen H., Fischer C.A., Langer J., Wiesinger M., Harder S.
Angewandte Chemie - International Edition ,
2019
66.
Shi X., Hou C., Zhao L., Deng P., Cheng J.
Chemical Communications ,
2020
67.
rcr_90_5_529bib67
Eaborn
2001
68.
rcr_90_5_529bib68
Eabom
J. Am. Chem. Soc. ,
1994
69.
10.1021/om960493+
70.
Köhler M., Koch A., Görls H., Westerhausen M.
Organometallics ,
2016
71.
Koch A., Wirgenings M., Krieck S., Görls H., Pohnert G., Westerhausen M.
Organometallics ,
2017
72.
rcr_90_5_529bib72
Eaborn
1997
73.
rcr_90_5_529bib73
Qi
Tetrahedron ,
2003
74.
rcr_90_5_529bib74
Hitchcock
1994
75.
rcr_90_5_529bib75
van den Hende
1995
76.
Crimmin M., Barrett A.G., Hill M., MacDougall D., Mahon M., Procopiou P.
Chemistry - A European Journal ,
2008
77.
Hitchcock P.B., Khvostov A.V., Lappert M.F.
Journal of Organometallic Chemistry ,
2002
78.
rcr_90_5_529bib78
Frankland
1996
79.
rcr_90_5_529bib79
Cloke
1991
80.
Hill M.S., Mahon M.F., Robinson T.P.
Chemical Communications ,
2010
81.
rcr_90_5_529bib81
Li
2019
82.
rcr_90_5_529bib82
Yan
J. Am. Chem. Soc. ,
2009
83.
Yan K., Schoendorff G., Upton B.M., Ellern A., Windus T.L., Sadow A.D.
Organometallics ,
2013
84.
Pindwal A., Ellern A., Sadow A.D.
Organometallics ,
2016
85.
Clegg W., Izod K., O'Shaughnessy P., Eaborn C., Smith J.D.
Angewandte Chemie - International Edition ,
1997
86.
Izod K., Liddle S.T., Clegg W.
Journal of the American Chemical Society ,
2003
87.
Coles M.P., Sözerli S.E., Smith J.D., Hitchcock P.B., Day I.J.
Organometallics ,
2009
88.
Bowman L.J., Izod K., Clegg W., Harrington R.W.
Organometallics ,
2007
89.
Hasinoff L., Takats J., Zhang X.W., Bond A.H., Rogers R.D.
Journal of the American Chemical Society ,
1994
90.
Zhang X.W., Maunder G.H., Gießmann S., MacDonald R., Ferguson M.J., Bond A.H., Rogers R.D., Sella A., Takats J.
Dalton Transactions ,
2011
91.
rcr_90_5_529bib91
Shi
Angew. Chem., Int. Ed. ,
2017
92.
rcr_90_5_529bib92
Hitchcock
2009
93.
rcr_90_5_529bib93
Liu
Chem. – Eur. J. ,
2013
94.
Liu X., Xiang L., Louyriac E., Maron L., Leng X., Chen Y.
Journal of the American Chemical Society ,
2018
95.
Liu X., Wen Q., Xiang L., Leng X., Chen Y.
Chemistry - A European Journal ,
2020
96.
Basalov I.V., Liu B., Roisnel T., Cherkasov A.V., Fukin G.K., Carpentier J., Sarazin Y., Trifonov A.A.
Organometallics ,
2016
97.
Shi X., Qin G., Wang Y., Zhao L., Liu Z., Cheng J.
Angewandte Chemie - International Edition ,
2019
98.
Cheng J., Takats J., Ferguson M.J., McDonald R.
Journal of the American Chemical Society ,
2008
99.
Ferrence G.M., Arduengo A.J., Jockisch A., Kim H., McDonald R., Takats J.
Journal of Alloys and Compounds ,
2006
100.
Ferrence G.M., McDonald R., Takats J.
Angewandte Chemie - International Edition ,
1999
101.
rcr_90_5_529bib101
Crimmin
2009
102.
Arrowsmith M., Hill M.S., Kociok-Köhn G.
Organometallics ,
2011
103.
Arrowsmith M., Hill M.S., Kociok-Köhn G.
Organometallics ,
2010
104.
Maitland B., Wiesinger M., Langer J., Ballmann G., Pahl J., Elsen H., Färber C., Harder S.
Angewandte Chemie - International Edition ,
2017
105.
Bellham P., Hill M.S., Kociok-Köhn G., Liptrot D.J.
Dalton Transactions ,
2013
106.
Bellham P., Hill M.S., Liptrot D.J., MacDougall D.J., Mahon M.F.
Chemical Communications ,
2011
107.
Nuclear magnetic resonance spectra of carbanions. Part 10. Dibenzyl-barium, -strontium, and -calcium
Takahashi K., Kondo Y., Asami R.
Journal of the Chemical Society Perkin Transactions 2 ,
1978
108.
Weeber A., Harder S., Brintzinger H.H., Knoll K.
Organometallics ,
2000
109.
Harder S., Müller S., Hübner E.
Organometallics ,
2003
110.
Wolf B.M., Stuhl C., Anwander R.
Chemical Communications ,
2018
111.
Schuhknecht D., Lhotzky C., Spaniol T.P., Maron L., Okuda J.
Angewandte Chemie - International Edition ,
2017
112.
Krieck S., Görls H., Westerhausen M.
Journal of the American Chemical Society ,
2010
113.
Izod K., Waddell P.G.
Organometallics ,
2015
114.
Feil F., Harder S.
Organometallics ,
2000
115.
Fischer R., Gärtner M., Görls H., Westerhausen M.
Angewandte Chemie - International Edition ,
2006
116.
Schuhknecht D., Truong K., Spaniol T.P., Maron L., Okuda J.
Chemical Communications ,
2018
117.
Wooles A.J., Mills D.P., Lewis W., Blake A.J., Liddle S.T.
Dalton Transactions ,
2010
118.
rcr_90_5_529bib118
Wolf
Angew. Chem., Int. Ed. ,
2016
119.
Jochmann P., Davin J.P., Spaniol T.P., Maron L., Okuda J.
Angewandte Chemie - International Edition ,
2012
120.
Remarkable Stability of Metallocenes with Superbulky Ligands: Spontaneous Reduction of SmIII to SmII
Ruspic C., Moss J., Schürmann M., Harder S.
Angewandte Chemie - International Edition ,
2008
121.
rcr_90_5_529bib121
Orzechowski
2008
122.
Causero A., Elsen H., Ballmann G., Escalona A., Harder S.
Chemical Communications ,
2017
123.
Basalov I.V., Lyubov D.M., Fukin G.K., Shavyrin A.S., Trifonov A.A.
Angewandte Chemie - International Edition ,
2012
124.
Harder S., Feil F., Weeber A.
Organometallics ,
2001
125.
Feil F., Harder S.
Organometallics ,
2001
126.
Harder S., Ruspic C., Bhriain N.N., Berkermann F., Schürmann M.
Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences ,
2008
127.
Feil F., Müller C., Harder S.
Journal of Organometallic Chemistry ,
2003
128.
Harder S., Feil F.
Organometallics ,
2002
129.
Harder S., Feil F., Knoll K.
Angewandte Chemie - International Edition ,
2001
130.
rcr_90_5_529bib130
Piesik
2007
131.
Selikhov A.N., Mahrova T.V., Cherkasov A.V., Fukin G.K., Maron L., Trifonov A.A.
Chemistry - A European Journal ,
2016
132.
Harder S.
Angewandte Chemie - International Edition ,
2003
133.
Harder S., Brettar J.
Angewandte Chemie - International Edition ,
2006
134.
Selikhov A.N., Lyubov D.M., Mahrova T.V., Cherkasov A.V., Fukin G.K., Trifonov A.A.
Russian Chemical Bulletin ,
2020
135.
rcr_90_5_529bib135
Shi
Dalton Trans. ,
2019
136.
Bordwell F.G.
Accounts of Chemical Research ,
1988
137.
Alexander J.S., Ruhlandt-Senge K.
Chemistry - A European Journal ,
2004
138.
Guino-o M.A., Torvisco A., Teng W., Ruhlandt-Senge K.
Inorganica Chimica Acta ,
2012
139.
le Coz E., Roueindeji H., Dorcet V., Roisnel T., Carpentier J., Sarazin Y.
Dalton Transactions ,
2019
140.
Selikhov A.N., Plankin G.S., Cherkasov A.V., Shavyrin A.S., Louyriac E., Maron L., Trifonov A.A.
Inorganic Chemistry ,
2019
141.
Selikhov A.N., Shavyrin A.S., Cherkasov A.V., Fukin G.K., Trifonov A.A.
Organometallics ,
2019
142.
Khristolyubov D.O., Lyubov D.M., Shavyrin A.S., Cherkasov A.V., Fukin G.K., Trifonov A.A.
Inorganic Chemistry Frontiers ,
2020
143.
Schumann H., Freckmann D.M., Dechert S.
Organometallics ,
2006
144.
Khristolyubov D.O., Lyubov D.M., Cherkasov A.V., Fukin G.K., Shavyrin A.S., Trifonov A.A.
Organometallics ,
2018
145.
Spielmann J., Harder S.
Chemistry - A European Journal ,
2007
146.
Shi X., Cheng J.
Dalton Transactions ,
2019
147.
Bochkarev L.N., Molosnova N.E., Zakharov L.N., Fukin G.K., Yanovsky A.I., Struckhov Y.T.
Journal of Organometallic Chemistry ,
1995
148.
Alexander J.S., Ruhlandt-Senge K., Hope H.
Organometallics ,
2003
149.
Alexander J.S., Ruhlandt-Senge K.
Angewandte Chemie - International Edition ,
2001
150.
Stevenson C.D., Peterson R.A.
Journal of Organic Chemistry ,
1984
151.
de Bruin-Dickason C.N., Boutland A.J., Dange D., Deacon G.B., Jones C.
Dalton Transactions ,
2018
152.
Freitag B., Pahl J., Färber C., Harder S.
Organometallics ,
2018
153.
Brinkmann C., Barrett A.G., Hill M.S., Procopiou P.A.
Journal of the American Chemical Society ,
2012
154.
Beletskaya I.P., Nájera C., Yus M.
Russian Chemical Reviews ,
2020
155.
Beletskaya I.P., Naájera C., Yus M.
Russian Chemical Reviews ,
2020
156.
Beletskaya I.P., Nájera C., Yus M.
Russian Chemical Reviews ,
2021
157.
Penafiel J., Maron L., Harder S.
Angewandte Chemie - International Edition ,
2014