Home / Articles / Cyclization of ortho-ethynylbiaryls as an emerging versatile tool for the construction of polycyclic arenes

Cyclization of ortho-ethynylbiaryls as an emerging versatile tool for the construction of polycyclic arenes

Alena Sergeevna Pankova 1
Alena Sergeevna Pankova
, 
Aleksandr Nikolaevich Shestakov 1
Aleksandr Nikolaevich Shestakov
, 
Mikhail Anatol'evich Kuznetsov 1
Mikhail Anatol'evich Kuznetsov
1 Institute of Chemistry, Saint Petersburg State University
Published 30 November 2018
28
Share
Cite this
GOST
 | 
Cite this
GOST
Pankova A. S., Shestakov A. N., Kuznetsov M. A. Cyclization of ortho-ethynylbiaryls as an emerging versatile tool for the construction of polycyclic arenes // Russian Chemical Reviews. 2018. Vol. 88. No. 6. pp. 594-643.
GOST all authors (up to 50)
Pankova A. S., Shestakov A. N., Kuznetsov M. A. Cyclization of ortho-ethynylbiaryls as an emerging versatile tool for the construction of polycyclic arenes // Russian Chemical Reviews. 2018. Vol. 88. No. 6. pp. 594-643.
RIS
 | 
Cite this
RIS
TY - JOUR
DO - 10.1070/RCR4855
UR - https://rcr.colab.ws/publications/10.1070/RCR4855
TI - Cyclization of ortho-ethynylbiaryls as an emerging versatile tool for the construction of polycyclic arenes
T2 - Russian Chemical Reviews
AU - Pankova, Alena Sergeevna
AU - Shestakov, Aleksandr Nikolaevich
AU - Kuznetsov, Mikhail Anatol'evich
PY - 2018
DA - 2018/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 594-643
IS - 6
VL - 88
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors)
@article{2018_Pankova,
author = {Alena Sergeevna Pankova and Aleksandr Nikolaevich Shestakov and Mikhail Anatol'evich Kuznetsov},
title = {Cyclization of ortho-ethynylbiaryls as an emerging versatile tool for the construction of polycyclic arenes},
journal = {Russian Chemical Reviews},
year = {2018},
volume = {88},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RCR4855},
number = {6},
pages = {594--643},
doi = {10.1070/RCR4855}
}
MLA
Cite this
MLA
Pankova, Alena Sergeevna, et al. “Cyclization of ortho-ethynylbiaryls as an emerging versatile tool for the construction of polycyclic arenes.” Russian Chemical Reviews, vol. 88, no. 6, Nov. 2018, pp. 594-643. https://rcr.colab.ws/publications/10.1070/RCR4855.
Views / Visits / Downloads
46 / 45 / 10

Abstract

Cyclization and cycloisomerization of ortho-aryl(ethynyl)arenes provide an easy direct access to fused polycyclic aromatic carbo- and heterocycles. This methodology has demonstrated an impressive progress in the recent years. The goal of this review is to give a comprehensive outlook on the synthetic potential, scope, limitations, and mechanistic aspects of the cyclization reactions. The material is arranged according to the activation method that can be used to induce cyclization: pyrolysis, metal catalysis, electrophilic activation, radical induction, base catalysis. Particular attention is paid to the specificity of ortho-ethynylbiaryls with a heterocyclic central core. The bibliography includes 257 references.

Funders

Russian Science Foundation
18-73-00089

References

1.
Novel Pd(II)- and Pt(II)-Catalyzed Regio- and Stereoselective trans-Hydroarylation of Alkynes by Simple Arenes
Jia C., Lu W., Oyamada J., Kitamura T., Matsuda K., Irie M., Fujiwara Y.
Journal of the American Chemical Society , 2000
2.
Efficient Activation of Aromatic C-H Bonds for Addition to C-C Multiple Bonds
Jia C., Piao D., Oyamada J., Lu W., Kitamura T., Fujiwara Y.
Science , 2000
3.
Catalytic Functionalization of Arenes and Alkanes via C−H Bond Activation
Jia C., Kitamura T., Fujiwara Y.
Accounts of Chemical Research , 2001
4.
rcr_88_6_594_bib4
Brown
1974
5.
rcr_88_6_594_bib5
Brown
Aust. J. Chem. , 1974
7.
rcr_88_6_594_bib7
Zimmermann
2001
8.
rcr_88_6_594_bib8
Nevado
2005
9.
rcr_88_6_594_bib9
Yamamoto
2009
10.
Acceleration of Conjugated Dienyne Cycloaromatization
Hitt D.M., O’Connor J.M.
Chemical Reviews , 2011
11.
rcr_88_6_594_bib11
de Mendoza
2012
13.
Alkenylation of Arenes and Heteroarenes with Alkynes
Boyarskiy V.P., Ryabukhin D.S., Bokach N.A., Vasilyev A.V.
Chemical Reviews , 2016
14.
1,3-Dien-5-ynes: Versatile Building Blocks for the Synthesis of Carbo- and Heterocycles
Aguilar E., Sanz R., Fernández-Rodríguez M.A., García-García P.
Chemical Reviews , 2016
15.
rcr_88_6_594_bib15
Yamamoto
2016
16.
Gold as a catalyst. Part II. Alkynes in the reactions of carbon - Carbon bond formation
17.
Umlagerung von Azulen in Naphthalin
Heilbronner E., Plattner P.A., Wieland K.
Cellular and Molecular Life Sciences , 1947
19.
Microwave Flash Pyrolysis
Cho H.Y., Ajaz A., Himali D., Waske P.A., Johnson R.P.
Journal of Organic Chemistry , 2009
20.
Corannulene. A convenient new synthesis
Scott L.T., Hashemi M.M., Meyer D.T., Warren H.B.
Journal of the American Chemical Society , 1991
21.
rcr_88_6_594_bib21
Scott
J. Am. Chem. Soc. , 1997
23.
Synthesis and Characterization of Hepta[5][5]circulene as a Subunit of C70Fullerene
Matsuda M., Matsubara H., Sato M., Okamoto S., Yamamoto K.
Chemistry Letters , 1996
24.
Application of flash vacuum pyrolysis to the synthesis of sulfur-containing heteroaromatic systems
Imamura K., Hirayama D., Yoshimura H., Takimiya K., Aso Y., Otsubo T.
Tetrahedron Letters , 1999
28.
Total Synthesis of Dendrochrysanene through a Frame Rearrangement
Katsuki N., Isshiki S., Fukatsu D., Okamura J., Kuramochi K., Kawabata T., Tsubaki K.
Journal of Organic Chemistry , 2017
29.
ipso-Cyclization: an emerging tool for multifunctional spirocyclohexadienones
Reddy C.R., Prajapti S.K., Warudikar K., Ranjan R., Rao B.B.
Organic and Biomolecular Chemistry , 2017
30.
rcr_88_6_594_bib30
Ngwira
2017
32.
Attenuation of London Dispersion in Dichloromethane Solutions
Pollice R., Bot M., Kobylianskii I.J., Shenderovich I., Chen P.
Journal of the American Chemical Society , 2017
33.
Enantioselective Total Synthesis and Biological Evaluation of (+)-Kibdelone A and a Tetrahydroxanthone Analogue
Winter D.K., Endoma-Arias M.A., Hudlicky T., Beutler J.A., Porco J.A.
Journal of Organic Chemistry , 2013
35.
Converting homogeneous to heterogeneous in electrophilic catalysis using monodisperse metal nanoparticles
Witham C.A., Huang W., Tsung C., Kuhn J.N., Somorjai G.A., Toste F.D.
Nature Chemistry , 2009
36.
Exploiting the π-acceptor properties of carbene-stabilized phosphorus centered trications [L3P]3+: applications in Pt(II) catalysis.
37.
Coordination Chemistry of Cyclopropenylidene-Stabilized Phosphenium Cations: Synthesis and Reactivity of Pd and Pt Complexes
Kozma Á., Deden T., Carreras J., Wille C., Petuškova J., Rust J., Alcarazo M.
Chemistry - A European Journal , 2014
38.
Pt-Catalyzed Enantioselective Cycloisomerization for the Synthesis of Planar-Chiral Ferrocene Derivatives
39.
Synthesis, docking, and biological studies of phenanthrene β-diketo acids as novel HIV-1 integrase inhibitors
Sharma H., Sanchez T.W., Neamati N., Detorio M., Schinazi R.F., Cheng X., Buolamwini J.K.
Bioorganic and Medicinal Chemistry Letters , 2013
40.
Rh-Mediated Enantioselective Synthesis, Crystal Structures, and Photophysical/Chiroptical Properties of Phenanthrenol-Based [9]Helicene-like Molecules
Yamano R., Hara J., Murayama K., Sugiyama H., Teraoka K., Uekusa H., Kawauchi S., Shibata Y., Tanaka K.
Organic Letters , 2016
46.
Toward Cove-Edged Low Band Gap Graphene Nanoribbons
Liu J., Li B., Tan Y., Giannakopoulos A., Sanchez-Sanchez C., Beljonne D., Ruffieux P., Fasel R., Feng X., Müllen K.
Journal of the American Chemical Society , 2015
47.
Synthesis of Dibenzo[hi,st ]ovalene and Its Amplified Spontaneous Emission in a Polystyrene Matrix
Paternò G.M., Chen Q., Wang X., Liu J., Motti S.G., Petrozza A., Feng X., Lanzani G., Müllen K., Narita A., Scotognella F.
Angewandte Chemie - International Edition , 2017
48.
Strong Exciton–Photon Coupling in a Nanographene Filled Microcavity
Coles D.M., Chen Q., Flatten L.C., Smith J.M., Müllen K., Narita A., Lidzey D.G.
Nano Letters , 2017
49.
Forty years of Clar's aromatic π-sextet rule
50.
An efficient synthesis of substituted chrysenes
Eccleshare L., Selzer S., Woodward S.
Tetrahedron Letters , 2017
51.
rcr_88_6_594_bib51
Liu
Angew. Chem., Int. Ed. , 2015
52.
Convenient Synthesis of Dibenzo[a,h]anthracenes and Picenes via C–H Arylation of Acetophenones with Arenediboronates
53.
Ph2N-Susbtituted Ethylene-Bridged p-Phenylene Oligomers: Synthesis and Photophysical and Redox Properties
Shaibu B.S., Lin S., Lin C., Wong K., Liu R.
Journal of Organic Chemistry , 2011
54.
Regiocontrolled Synthesis of Ethene-Bridgedpara-Phenylene Oligomers Based on PtII- and RuII-Catalyzed Aromatization
Chen T., Lee T., Lin M., Sohel S. ., Diau E.W., Lush S., Liu R.
Chemistry - A European Journal , 2010
56.
Synthesis and Resolution of Substituted [5]Carbohelicenes
Usui K., Yamamoto K., Shimizu T., Okazumi M., Mei B., Demizu Y., Kurihara M., Suemune H.
Journal of Organic Chemistry , 2015
57.
P-Type Photochromism of New Helical Naphthopyrans: Synthesis and Photochemical, Photophysical and Theoretical Study
Frigoli M., Marrot J., Gentili P.L., Jacquemin D., Vagnini M., Pannacci D., Ortica F.
ChemPhysChem , 2015
59.
Synthesis of Hexahelicene and 1-Methoxyhexahelicene via Cycloisomerization of Biphenylyl-Naphthalene Derivatives
Storch J., Sýkora J., Čermák J., Karban J., Císařová I., Růžička A.
Journal of Organic Chemistry , 2009
60.
Synthesis, Properties, and Two-Dimensional Adsorption Characteristics of 5-Amino[6]hexahelicene
van der Meijden M.W., Gelens E., Quirós N.M., Fuhr J.D., Gayone J.E., Ascolani H., Wurst K., Lingenfelder M., Kellogg R.M.
Chemistry - A European Journal , 2015
61.
rcr_88_6_594_bib61
van der Meijden
Chem. – Eur. J. , 2016
62.
Facile synthetic route to highly luminescent sila[7]helicene.
Oyama H., Nakano K., Harada T., Kuroda R., Naito M., Nobusawa K., Nozaki K.
Organic Letters , 2013
63.
Synthesis and Properties of [7]Helicene-like Compounds Fused with a Fluorene Unit
Oyama H., Akiyama M., Nakano K., Naito M., Nobusawa K., Nozaki K.
Organic Letters , 2016
64.
Synthesis of substituted pyrenes by indirect methods
Casas-Solvas J.M., Howgego J.D., Davis A.P.
Organic and Biomolecular Chemistry , 2014
65.
Equatorenes: Synthesis and Properties of Chiral Naphthalene, Phenanthrene, Chrysene, and Pyrene Possessing Bis(1-adamantyl) Groups at the Peri-position
Yamamoto K., Oyamada N., Xia S., Kobayashi Y., Yamaguchi M., Maeda H., Nishihara H., Uchimaru T., Kwon E.
Journal of the American Chemical Society , 2013
66.
rcr_88_6_594_bib66
Walker
2010
67.
2,6-Bis(phenylethynyl)biphenyls and Their Cyclization to Pyrenes
68.
On-Surface Annulation Reaction Cascade for the Selective Synthesis of Diindenopyrene
Eisenhut F., Lehmann T., Viertel A., Skidin D., Krüger J., Nikipar S., Ryndyk D.A., Joachim C., Hecht S., Moresco F., Cuniberti G.
ACS Nano , 2017
70.
rcr_88_6_594_bib70
Wu
J. Org. Chem. , 2012
72.
rcr_88_6_594_bib72
Shiotari
Nature Commun. , 2017
74.
Intramolecular Reactions of Alkynes with Furans and Electron Rich Arenes Catalyzed by PtCl2:  The Role of Platinum Carbenes as Intermediates
Martín-Matute B., Nevado C., Cárdenas D.J., Echavarren A.M.
Journal of the American Chemical Society , 2003
75.
rcr_88_6_594_bib75
Sarkar
2013
77.
rcr_88_6_594_bib77
Lim
2013
78.
The right way to self-fuse bi- and terpyrenyls to afford graphenic cutouts
Lorbach D., Wagner M., Baumgarten M., Müllen K.
Chemical Communications , 2013
79.
Effective synthesis of diiodinated picene and dibenzo[a,h]anthracene by AuCl-catalyzed double cyclization
Nakae T., Ohnishi R., Kitahata Y., Soukawa T., Sato H., Mori S., Okujima T., Uno H., Sakaguchi H.
Tetrahedron Letters , 2012
81.
rcr_88_6_594_bib81
Xie
2008
83.
Synthesis of Pyrenes by Twofold Hydroarylation of 2,6-Dialkynylbiphenyls
Matsuda T., Moriya T., Goya T., Murakami M.
Chemistry Letters , 2011
85.
Direct Synthesis of Fused Indoles by Gold-Catalyzed Cascade Cyclization of Diynes
Hirano K., Inaba Y., Takahashi N., Shimano M., Oishi S., Fujii N., Ohno H.
Journal of Organic Chemistry , 2011
87.
Gold(I)-Catalyzed Polycyclizations of Polyenyne-Type Anilines Based on Hydroamination and Consecutive Hydroarylation Cascade
Hirano K., Inaba Y., Takasu K., Oishi S., Takemoto Y., Fujii N., Ohno H.
Journal of Organic Chemistry , 2011
89.
Polyaromatic Ribbon/Benzofuran Fusion via Consecutive Endo Cyclizations of Enediynes
Byers P.M., Rashid J.I., Mohamed R.K., Alabugin I.V.
Organic Letters , 2012
91.
Design and synthesis of a novel class of CK2 inhibitors: application of copper- and gold-catalysed cascade reactions for fused nitrogen heterocycles
Suzuki Y., Oishi S., Takei Y., Yasue M., Misu R., Naoe S., Hou Z., Kure T., Nakanishi I., Ohno H., Hirasawa A., Tsujimoto G., Fujii N.
Organic and Biomolecular Chemistry , 2012
92.
rcr_88_6_594_bib92
Stoye
2015
93.
Synthesis of Substituted Naphtho-Ferrocenes via a Gold(I)-Catalyzed Intramolecular 6-endo -Dig Cyclization
94.
Mild access to planar-chiral ortho-condensed aromatic ferrocenes via gold(i)-catalyzed cycloisomerization of ortho-alkynylaryl ferrocenes
Urbano A., Hernández-Torres G., del Hoyo A.M., Martínez-Carrión A., Carmen Carreño M.
Chemical Communications , 2016
95.
Polycationic ligands in gold catalysis: synthesis and applications of extremely π-acidic catalysts.
Carreras J., Gopakumar G., Gu L., Gimeno A., Linowski P., Petuškova J., Thiel W., Alcarazo M.
Journal of the American Chemical Society , 2013
96.
Bis(cyclopropenium)phosphines: Synthesis, Reactivity, and Applications
Mehler G., Linowski P., Carreras J., Zanardi A., Dube J.W., Alcarazo M.
Chemistry - A European Journal , 2016
97.
Cyclopropenylylidene-Stabilized Diaryl and Dialkyl Phosphenium Cations: Applications in Homogeneous Gold Catalysis
98.
Synthesis and reactivity of α-cationic phosphines: the effect of imidazolinium and amidinium substituents
Haldón E., Kozma Á., Tinnermann H., Gu L., Goddard R., Alcarazo M.
Dalton Transactions , 2016
99.
Enantioselective Synthesis of [6]Carbohelicenes
González-Fernández E., Nicholls L.D., Schaaf L.D., Farès C., Lehmann C.W., Alcarazo M.
Journal of the American Chemical Society , 2017
100.
rcr_88_6_594_bib100
Pan
Chem. Commun. , 2014
102.
Exclusive 5-exo-dig hydroarylation of o-alkynyl biaryls proceeding via C-H activation pathway.
Chernyak N., Gevorgyan V.
Journal of the American Chemical Society , 2008
106.
Pd-catalyzed synthesis of 9,9'-bifluorenylidene derivatives via dual C-H activation of bis-biaryl alkynes.
Zhao J., Asao N., Yamamoto Y., Jin T.
Journal of the American Chemical Society , 2014
108.
Expeditious synthesis of tetrasubstituted helical alkenes by a cascade of palladium-catalyzed C-H activations.
110.
Palladium-Catalyzed Synthesis of Tetrasubstituted Olefins by Triple Domino Process
Naveen K., Nikson S.A., Perumal P.T.
Advanced Synthesis and Catalysis , 2017
112.
Three-component Pd/Cu-catalyzed cascade reactions of cyclic iodoniums, alkynes, and boronic acids: an approach to methylidenefluorenes.
113.
Copper-catalysed bromoalkynylation of arynes
Morishita T., Yoshida H., Ohshita J.
Chemical Communications , 2010
116.
Palladium(II)-catalyzed asymmetric cycloisomerization of enynes for axially chiral biaryl construction
117.
rcr_88_6_594_bib117
Fürstner
2003
118.
Evaluation of semiconducting molecular thin films solution-processed via the photoprecursor approach: the case of hexyl-substituted thienoanthracenes
Quinton C., Suzuki M., Kaneshige Y., Tatenaka Y., Katagiri C., Yamaguchi Y., Kuzuhara D., Aratani N., Nakayama K., Yamada H.
Journal of Materials Chemistry C , 2015
119.
Z-Shaped Pyrrolo[3,2-b ]pyrroles and Their Transformation into π-Expanded Indolo[3,2-b ]indoles
Stężycki R., Grzybowski M., Clermont G., Blanchard-Desce M., Gryko D.T.
Chemistry - A European Journal , 2016
120.
The Molecular Engineering of Organic Sensitizers for Solar-Cell Applications
Delcamp J.H., Yella A., Holcombe T.W., Nazeeruddin M.K., Grätzel M.
Angewandte Chemie - International Edition , 2012
121.
Approaches for Selective Synthesis of Ullazine Donor-Acceptor Systems
Drigo N.A., Paek S., Huckaba A.J., Schouwink P.A., Tabet N., Nazeeruddin M.K.
Chemistry - A European Journal , 2017
122.
Controlling charge-transfer properties through a microwave-assisted mono- or bis-annulation of dialkynyl-N-(het)arylpyrroles
123.
Expanding the scope of peropyrenes and teropyrenes through a facile InCl3-catalyzed multifold alkyne benzannulation
Yang W., Kazemi R.R., Karunathilake N., Catalano V.J., Alpuche-Aviles M.A., Chalifoux W.A.
Organic Chemistry Frontiers , 2018
124.
Ag(i)-Catalyzed cycloisomerization reactions: synthesis of substituted phenanthrenes and naphthothiophenes
Saunthwal R.K., Danodia A.K., Saini K.M., Verma A.K.
Organic and Biomolecular Chemistry , 2017
128.
10.1021/ja962684+
129.
rcr_88_6_594_bib129
Shen
J. Org. Chem. , 2005
131.
Cationic iron-catalyzed intramolecular alkyne-hydroarylation with electron-deficient arenes.
132.
Neodymium-catalyzed intramolecular alkyne-hydroarylation with arenes
Xu D., Jin R., Liu W., Ba F., Li Y., Ding A., Guo H.
Tetrahedron Letters , 2016
133.
AlCl3-Catalyzed Intramolecular Hydroarylation of Arenes with Alkynes
Guo H., Gu G., Li Y., Wang Y., Xu D., Jin R.
Synlett , 2017
134.
rcr_88_6_594_bib134
Wang
RSC Adv. , 2014
135.
Merging photoredox catalysis with Lewis acid catalysis: activation of carbon–carbon triple bonds
Jin R., Chen Y., Liu W., Xu D., Li Y., Ding A., Guo H.
Chemical Communications , 2016
136.
rcr_88_6_594_bib136
Jin
J. Org. Chem. , 2016
137.
CuBr2-promoted cyclization and bromination of arene–alkynes: C–Br bond formation via reductive elimination of Cu(iii) species
Liu W., Chen J., Jin R., Xu D., Li Y., Ba F., Gu G., Kuang Y., Guo H.
Organic Chemistry Frontiers , 2016
140.
Directed Electrophilic Cyclizations: Efficient Methodology for the Synthesis of Fused Polycyclic Aromatics
Goldfinger M.B., Crawford K.B., Swager T.M.
Journal of the American Chemical Society , 1997
141.
Synthesis of Ethynyl-Substituted Quinquephenyls and Conversion to Extended Fused-Ring Structures
Goldfinger M.B., Crawford K.B., Swager T.M.
Journal of Organic Chemistry , 1998
143.
Synthesis of J-Aggregating Dibenz[a,j]anthracene-Based Macrocycles
Chan J.M., Tischler J.R., Kooi S.E., Bulović V., Swager T.M.
Journal of the American Chemical Society , 2009
144.
Adding Four Extra K-Regions to Hexa-peri-hexabenzocoronene
Dumslaff T., Yang B., Maghsoumi A., Velpula G., Mali K.S., Castiglioni C., De Feyter S., Tommasini M., Narita A., Feng X., Müllen K.
Journal of the American Chemical Society , 2016
146.
Synthesis of polycyclic aromatics and heteroaromatics via electrophilic cyclization.
Yao T., Campo M.A., Larock R.C.
Journal of Organic Chemistry , 2005
148.
Nickel-Catalyzed Alkynylation of Anisoles via C–O Bond Cleavage
Tobisu M., Takahira T., Ohtsuki A., Chatani N.
Organic Letters , 2015
151.
rcr_88_6_594_bib151
Feng
J. Am. Chem. Soc. , 2007
152.
Triangle-Shaped Polycyclic Aromatic Hydrocarbons
Feng X., Wu J., Ai M., Pisula W., Zhi L., Rabe J., Müllen K.
Angewandte Chemie - International Edition , 2007
154.
Synthesis of Stair-Stepped Polymers Containing Dibenz[a,h]anthracene Subunits
155.
Functionalized Dibenzo[g,p]chrysenes: Variable Photophysical and Electronic Properties and Liquid−Crystal Chemistry
Chaudhuri R., Hsu M., Li C., Wang C., Chen C., Lai C.K., Chen L., Liu S., Wu C., Liu R.
Organic Letters , 2008
157.
Synthesis and Properties of Ethylene-Annulated Di(perylene diimides)
Li Y., Wang C., Li C., Di Motta S., Negri F., Wang Z.
Organic Letters , 2012
158.
rcr_88_6_594_bib158
Mohamed
Angew. Chem., Int. Ed. , 2016
159.
Electrospun Nanofibrous Film Doped with a Conjugated Polymer for DNT Fluorescence Sensor
Long Y., Chen H., Yang Y., Wang H., Yang Y., Li N., Li K., Pei J., Liu F.
Macromolecules , 2009
160.
Unexpected Scholl Reaction of 6,7,13,14-Tetraarylbenzo[k]tetraphene: Selective Formation of Five-Membered Rings in Polycyclic Aromatic Hydrocarbons
Liu J., Narita A., Osella S., Zhang W., Schollmeyer D., Beljonne D., Feng X., Müllen K.
Journal of the American Chemical Society , 2016
161.
Fused Dibenzo[a,m]rubicene: A New Bowl-Shaped Subunit of C70 Containing Two Pentagons
Liu J., Osella S., Ma J., Berger R., Beljonne D., Schollmeyer D., Feng X., Müllen K.
Journal of the American Chemical Society , 2016
163.
Electron-transporting PAHs with dual perylenediimides: syntheses and semiconductive characterizations
167.
Expedient Iodocyclization Approach Toward Polysubstituted 3H-Benzo[e]indoles
Martins G.M., Zeni G., Back D.F., Kaufman T.S., Silveira C.C.
Advanced Synthesis and Catalysis , 2015
170.
rcr_88_6_594_bib170
Chen
J. Org. Chem. , 2011
172.
Benziodoxole Triflate as a Versatile Reagent for Iodo(III)cyclization of Alkynes
173.
Discovery of Stabilized Bisiodonium Salts as Intermediates in the Carbon-Carbon Bond Formation of Alkynes
Dohi T., Kato D., Hyodo R., Yamashita D., Shiro M., Kita Y.
Angewandte Chemie - International Edition , 2011
174.
Contorted Arene‐fused Metallophthalocyanines
Suzuki H., Kobayashi N., Kimura M.
Asian Journal of Organic Chemistry , 2016
176.
Microwave-assisted synthesis of 4,9-linked pyrene-based ladder conjugated polymers
Shen X., Wu Y., Bai L., Zhao H., Ba X.
Journal of Polymer Science, Part A: Polymer Chemistry , 2017
178.
rcr_88_6_594_bib178
Yang
Angew. Chem., Int. Ed. , 2016
179.
New thiophene-functionalized pyrene, peropyrene, and teropyrene via a two- or four-fold alkyne annulation and their photophysical properties
181.
Bottom-Up Synthesis of Soluble and Narrow Graphene Nanoribbons Using Alkyne Benzannulations
Yang W., Lucotti A., Tommasini M., Chalifoux W.A.
Journal of the American Chemical Society , 2016
182.
rcr_88_6_594_bib182
Yang
J. Am. Chem. Soc. , 2017
184.
rcr_88_6_594_bib184
Akbar
2013
185.
Formation of C(sp2)Boronate Esters by Borylative Cyclization of Alkynes Using BCl3
Warner A.J., Lawson J.R., Fasano V., Ingleson M.J.
Angewandte Chemie - International Edition , 2015
186.
Regio- and Stereoselective Chlorocyanation of Alkynes
Barrado A.G., Zieliński A., Goddard R., Alcarazo M.
Angewandte Chemie - International Edition , 2017
187.
Metal-Free Electrophilic Phosphination/Cyclization of Alkynes
Unoh Y., Hirano K., Miura M.
Journal of the American Chemical Society , 2017
188.
Palladium-catalyzed iodine-mediated electrophilic annulation of 2-(1-alkynyl)biphenyls with disulfides.
189.
rcr_88_6_594_bib189
Scott
2004
190.
Synthesis of Functionalized Phenanthrenes via Regioselective Oxidative Radical Cyclization
Pati K., Michas C., Allenger D., Piskun I., Coutros P.S., Gomes G.D., Alabugin I.V.
Journal of Organic Chemistry , 2015
191.
Solvent dependent photocyclization and photophysics of some 2-ethynylbiphenyls
Lewis F.D., Karagiannis P.C., Sajimon M.C., Lovejoy K.S., Zuo X., Rubin M., Gevorgyan V.
Photochemical and Photobiological Sciences , 2006
192.
Photoinduced Intramolecular Haloarylation and Hydroarylation of Alkynes
Xu D., Rios R., Ba F., Ma D., Gu G., Ding A., Kuang Y., Guo H.
Asian Journal of Organic Chemistry , 2016
193.
Sulfonyl radical-enabled 6-endo-trig cyclization for regiospecific synthesis of unsymmetrical diaryl sulfones
Fu R., Hao W., Wu Y., Wang N., Tu S., Li G., Jiang B.
Organic Chemistry Frontiers , 2016
194.
rcr_88_6_594_bib194
Yamaguchi
J. Am. Chem. Soc. , 2001
195.
Liquid Crystalline Coronene Derivatives with Extraordinary Fluorescence Properties
Rohr U., Schlichting P., Böhm A., Gross M., Meerholz K., Bräuchle C., Müllen K.
Angewandte Chemie - International Edition , 1998
198.
Liquid crystalline coronene derivatives
Rohr U., Kohl C., Müllen K., van de Craats A., Warman J.
Journal of Materials Chemistry A , 2001
199.
New hydrosoluble perylene and coronene derivatives
Franceschin M., Alvino A., Ortaggi G., Bianco A.
Tetrahedron Letters , 2004
200.
Synthesis and Self-Organization of Core-Extended Perylene Tetracarboxdiimides with Branched Alkyl Substituents
Nolde F., Pisula W., Müller S., Kohl C., Müllen K.
Chemistry of Materials , 2006
201.
Specific interactions with intra- and intermolecular G-quadruplex DNA structures by hydrosoluble coronene derivatives: A new class of telomerase inhibitors
Franceschin M., Alvino A., Casagrande V., Mauriello C., Pascucci E., Savino M., Ortaggi G., Bianco A.
Bioorganic and Medicinal Chemistry , 2007
202.
Room-temperature discotic liquid-crystalline coronene diimides exhibiting high charge-carrier mobility in air
An Z., Yu J., Domercq B., Jones S.C., Barlow S., Kippelen B., Marder S.R.
Journal of Materials Chemistry A , 2009
203.
Supramolecular Assemblies Formed on an Epitaxial Graphene Superstructure
Pollard A., Perkins E., Smith N., Saywell A., Goretzki G., Phillips A., Argent S., Sachdev H., Müller F., Hüfner S., Gsell S., Fischer M., Schreck M., Osterwalder J., Greber T., et. al.
Angewandte Chemie - International Edition , 2010
204.
Aromatic Core Extension in the Series of N-Cyclic Bay-Substituted Perylene G-Quadruplex Ligands: Increased Telomere Damage, Antitumor Activity, and Strong Selectivity for Neoplastic over Healthy Cells
Franceschin M., Rizzo A., Casagrande V., Salvati E., Alvino A., Altieri A., Ciammaichella A., Iachettini S., Leonetti C., Ortaggi G., Porru M., Bianco A., Biroccio A.
ChemMedChem , 2012
205.
rcr_88_6_594_bib205
Zhao
Chem. – Eur. J. , 2015
206.
rcr_88_6_594_bib206
Zhu
Adv. Mater. , 2016
208.
rcr_88_6_594_bib208
Lee
J. Mater. Chem. C , 2016
209.
Synthesis and characterization of π-extended thienoacenes with up to 13 fused aromatic rings
Shao J., Zhao X., Wang L., Tang Q., Li W., Yu H., Tian H., Zhang X., Geng Y., Wang F.
Tetrahedron Letters , 2014
211.
Highly Luminous Sky-Blue Organic Light-Emitting Diodes Based on the Bis[(1,2)(5,6)]indoloanthracene Emissive Layer
Ivaniuk K., Cherpak V., Stakhira P., Hotra Z., Minaev B., Baryshnikov G., Stromylo E., Volyniuk D., Grazulevicius J.V., Lazauskas A., Tamulevicius S., Witulski B., Light M.E., Gawrys P., Whitby R.J., et. al.
Journal of Physical Chemistry C , 2016
212.
Nine-ring angular fused biscarbazoloanthracene displaying a solid state based excimer emission suitable for OLED application
Baryshnikov G.V., Gawrys P., Ivaniuk K., Witulski B., Whitby R.J., Al-Muhammad A., Minaev B., Cherpak V., Stakhira P., Volyniuk D., Wiosna-Salyga G., Luszczynska B., Lazauskas A., Tamulevicius S., Grazulevicius J.V., et. al.
Journal of Materials Chemistry C , 2016
213.
Concise synthesis of tylophorine
215.
Synthesis of 2-Aza[6]helicene and Attempts To Synthesize 2,14-Diaza[6]helicene Utilizing Metal-Catalyzed Cycloisomerization
Storch J., Čermák J., Karban J., Císařová I., Sýkora J.
Journal of Organic Chemistry , 2010
216.
Cycloisomerization – a straightforward way to benzo[h]quinolines and benzo[c]acridines
Shestakov A.N., Pankova A.S., Kuznetsov M.A.
Chemistry of Heterocyclic Compounds , 2017
217.
Aza-Annulation of Enynyl Azides: A New Approach to Substituted Pyridines
Raji Reddy C., Panda S.A., Reddy M.D.
Organic Letters , 2015
218.
Synthesis of pyrrolo[1,2-a]naphthyridines by Lewis acid mediated cycloisomerization
Flader A., Parpart S., Ehlers P., Langer P.
Organic and Biomolecular Chemistry , 2017
219.
Synthesis and Properties of Aza-ullazines
Boldt S., Parpart S., Villinger A., Ehlers P., Langer P.
Angewandte Chemie - International Edition , 2017
221.
Rh(III)-catalyzed C-H bond activation along with "rollover" for the synthesis of 4-azafluorenes.
224.
Brønsted acid mediated cyclizations of ortho-aryl(ethynyl)pyrimidines
Shestakov A.N., Pankova A.S., Golubev P., Khlebnikov A.F., Kuznetsov M.A.
Tetrahedron , 2017
225.
rcr_88_6_594_bib225
Gulevskaya
2016
226.
rcr_88_6_594_bib226
Zhang
J. Am. Chem. Soc. , 2005
227.
Palladium-Catalyzed Intramolecular Fujiwara-Hydroarylation: Synthesis of Benzo[a]phenazines Derivatives
Kumar S., Saunthwal R.K., Mujahid M., Aggarwal T., Verma A.K.
Journal of Organic Chemistry , 2016
228.
Metal catalyst free cyclization of 3-alkynyl substituted 2-(indol-3-yl)quinoxalines in TFA alone: a new synthesis of indolophenazines
Kumar K.S., Bhaskar B., Ramulu M.S., Kumar N.P., Ashfaq M.A., Pal M.
Organic and Biomolecular Chemistry , 2017
229.
Indolizino[5,6-b]quinoxaline Derivatives: Intramolecular Charge Transfer Characters and NIR Fluorescence
Kojima M., Hayashi H., Aotake T., Ikeda S., Suzuki M., Aratani N., Kuzuhara D., Yamada H.
Chemistry - An Asian Journal , 2015
230.
Regioselective 6-endo-dig iodocyclization: an accessible approach for iodo-benzo[a]phenazines
Kumar S., Mujahid M., Verma A.K.
Organic and Biomolecular Chemistry , 2017
231.
rcr_88_6_594_bib231
Gulevskaya
2018
232.
rcr_88_6_594_bib232
Dong
Adv. Mater. , 2013
233.
Electron Transport Materials for Organic Light-Emitting Diodes
Kulkarni A.P., Tonzola C.J., Babel A., Jenekhe S.A.
Chemistry of Materials , 2004
235.
Heterotetracenes: Flexible Synthesis and in Silico Assessment of the Hole-Transport Properties
Li Y., Gryn'ova G., Saenz F., Jeanbourquin X., Sivula K., Corminboeuf C., Waser J.
Chemistry - A European Journal , 2017
237.
Sequential Electrophilic and Photochemical Cyclizations from Bis(bithienyl)acetylene to a Tetrathienonaphthalene Core
Dou C., Saito S., Gao L., Matsumoto N., Karasawa T., Zhang H., Fukazawa A., Yamaguchi S.
Organic Letters , 2012
239.
Synthesis and Isomeric Effects of Ladder-Type Alkylated Terbenzodithiophene Derivatives
Chen Y., Hsu J., Lin F., Lai Y., Chou H., Cheng Y.
Journal of Organic Chemistry , 2016
241.
Synthesis and Properties of Ethene-Bridged Terthiophenes
Mitsudo K., Sato H., Yamasaki A., Kamimoto N., Goto J., Mandai H., Suga S.
Organic Letters , 2015
242.
Synthesis of a 4,9-Didodecyl Angular-Shaped Naphthodiselenophene Building Block To Achieve High-Mobility Transistors
Tsai C., Yu R., Lin F., Lai Y., Hsu J., Cheng S., Hsu C., Cheng Y.
Chemistry of Materials , 2016
243.
Synthesis-driven mapping of the dictyodendrin alkaloids
Buchgraber P., Domostoj M.M., Scheiper B., Wirtz C., Mynott R., Rust J., Fürstner A.
Tetrahedron , 2009
244.
Divergent C-H Annulation for Multifused N-Heterocycles: Regio- and Stereospecific Cyclizations of N-Alkynylindoles
Alam K., Hong S.W., Oh K.H., Park J.K.
Angewandte Chemie - International Edition , 2017
245.
Pd-NHC-Catalyzed Alkynylation of General Aryl Sulfides with Alkynyl Grignard Reagents
Baralle A., Yorimitsu H., Osuka A.
Chemistry - A European Journal , 2016
247.
rcr_88_6_594_bib247
Fan
J. Org. Chem. , 2015
250.
rcr_88_6_594_bib250
Rustagi
2012
251.
rcr_88_6_594_bib251
Dyker
2000
252.
Gvozdev Valentin Dmitrievich, Shavrin Konstantin Nikolaevich, Baskir Esfir Grigor'evna, Egorov Mikhail Petrovich, Nefedov Oleg Matveevich
Mendeleev Communications , 2017
253.
rcr_88_6_594_bib253
Zhou
2012
255.
Unprecedented synthesis of 1,2,3-triazolo-cinnolinone via Sonogashira coupling and intramolecular cyclization
Kumar A., Tiwari D.K., Sridhar B., Likhar P.R.
Organic and Biomolecular Chemistry , 2018
257.
Oxidative Intramolecular 1,2‐Amino‐Oxygenation of Alkynes under Au I /Au III Catalysis: Discovery of a Pyridinium‐Oxazole Dyad as an Ionic Fluorophore
Shaikh A.C., Ranade D.S., Rajamohanan P.R., Kulkarni P.P., Patil N.T.
Angewandte Chemie - International Edition , 2016