Rhodium(III)-catalyzed Mono- and Dialkenylation of N-Phenyl-7-azaindoles via Regioselective C-H Bond Cleavage

被引：7

作者：

Morioka, Ryosuke ^{[1
]}

Satoh, Tetsuya ^{[1
,2
]}

Miura, Masahiro ^{[1
]}

机构：

[1] Osaka Univ, Grad Sch Engn, Dept Appl Chem, 2-2 Yamadaoka, Suita, Osaka 5650871, Japan

[2] Osaka City Univ, Grad Sch Sci, Dept Chem, Sumiyoshi Ku, 3-3-138 Sugimoto, Osaka 5588585, Japan

来源：

CHEMISTRY LETTERS | 2016年 / 45卷 / 06期

关键词：

C-H bond functionalization; Rhodium; Directing group; CATALYZED OXIDATIVE COUPLING/CYCLIZATION; CONJUGATED POLYMERS; COUPLING REACTIONS; INTERNAL ALKYNES; ALKENYLATION; RUTHENIUM; PHENYLAZOLES; FUNCTIONALIZATION; BENZYLAMINES; 7-AZAINDOLES;

D O I：

10.1246/cl.160234

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Rhodium-catalyzed regioselective mono- and dialkenylation reactions of N-phenyl-7-azaindoles with alkenes proceed efficiently under rhodium(III) catalysis. The one-pot synthesis of unsymmetrically dialkenylated benzene derivative can also be achieved. Some of the alkenylated products exhibit solid-state fluorescence.

引用

页码：682 / 684

页数：3

共 47 条

[1] Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope
Ackermann, Lutz
[J]. CHEMICAL REVIEWS, 2011, 111 (03) : 1315 - 1345
[2] Alonso JA, 2014, BIOORG MED CHEM LETT, V24, P5127, DOI 10.1016/j.bmcl.2014.08.028
[3] Rhodium-catalyzed Intramolecular Dehydrogenatiye Aryl-Aryl Coupling Using Air as Terminal Oxidant
Baars, Hannah
Unoh, Yuto
Okada, Takeshi
Hirano, Koji
Satoh, Tetsuya
Tanaka, Ken
Bolm, Carsten
Miura, Masahiro
[J]. CHEMISTRY LETTERS, 2014, 43 (11) : 1782 - 1784
[4] Nickel Catalysts/N,N′-Bidentate Directing Groups: An Excellent Partnership in Directed C-H Activation Reactions
Castro, Luis C. Misal
Chatani, Naoto
[J]. CHEMISTRY LETTERS, 2015, 44 (04) : 410 - 421
[5] Recent advances in the transition metal-catalyzed twofold oxidative C-H bond activation strategy for C-C and C-N bond formation
Cho, Seung Hwan
Kim, Ji Young
Kwak, Jaesung
Chang, Sukbok
[J]. CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) : 5068 - 5083
[6] Rhodium Catalyzed Chelation-Assisted C-H Bond Functionalization Reactions
Colby, Denise A.
Tsai, Andy S.
Bergman, Robert G.
Ellman, Jonathan A.
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) : 814 - 825
[7] Palladium- and Copper-Catalyzed Arylation of Carbon-Hydrogen Bonds
Daugulis, Olafs
Do, Hien-Quang
Shabashov, Dmitry
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (08) : 1074 - 1086
[8] Weak Coordination as a Powerful Means for Developing Broadly Useful C-H Functionalization Reactions
Engle, Keary M.
Mei, Tian-Sheng
Wasa, Masayuki
Yu, Jin-Quan
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) : 788 - 802
[9] Rhodium-catalyzed oxidative coupling of aromatic imines with internal alkynes via regioselective C-H bond cleavage
Fukutani, Tatsuya
Umeda, Nobuyoshi
Hirano, Koji
Satoh, Tetsuya
Miura, Masahiro
[J]. CHEMICAL COMMUNICATIONS, 2009, (34) : 5141 - 5143
[10] Synthesis of Light-Emitting Conjugated Polymers for Applications in Electroluminescent Devices
Grimsdale, Andrew C.
Chan, Khai Leok
Martin, Rainer E.
Jokisz, Pawel G.
Holmes, Andrew B.
[J]. CHEMICAL REVIEWS, 2009, 109 (03) : 897 - 1091

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