Rhodium(III)- and Iridium(III)-Catalyzed C7 Alkylation of Indolines with Diazo Compounds

被引：150

作者：

Ai, Wen ^{[1
,2
,3
]}

Yang, Xueyan ^{[2
,3
]}

Wu, Yunxiang ^{[1
]}

Wang, Xuan ^{[1
]}

Li, Yuanchao ^{[1
]}

Yang, Yaxi ^{[1
]}

Zhou, Bing ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Mat Med, Dept Med Chem, Shanghai 201203, Peoples R China

[2] E China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China

[3] E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2014年 / 20卷 / 52期

基金：

中国国家自然科学基金;

关键词：

alkylation; C-H activation; indolines; iridium; rhodium; H BOND ALKYLATION; CARBENOID FUNCTIONALIZATION; N-TOSYLHYDRAZONES; METAL CARBENE; ARYLATION; INDOLES; ALKENES; ALKYNES; ALKYNYLATION; ALKALOIDS;

D O I：

10.1002/chem.201405077

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A Rh-III-catalyzed procedure for the C7-selective C-H alkylation of various indolines with alpha-diazo compounds at room temperature is reported. The advantages of this process are: 1) simple, mild, and pH-neutral reaction conditions, 2) broad substrate scope, 3) complete regioselectivity, 4) no need for an external oxidant, and 5) N-2 as the sole by-product. Furthermore, alkylation and bis-alkylation of carbazoles at the C1 and C8 positions have also been developed. More significantly, for the first time, a successful Ir-III-catalyzed intermolecular insertion of arene C-H bonds into a-diazo compounds is reported.

引用

页码：17653 / 17657

页数：5

共 85 条

[1] Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].

Ackermann, Lutz .

CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345

[2]

[Anonymous], 2011, Angew. Chem.

[3] Tosylhydrazones: New Uses for Classic Reagents in Palladium-Catalyzed Cross-Coupling and Metal-Free Reactions [J].

Barluenga, Jose ;

Valdes, Carlos .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (33) :7486-7500

[4] Palladium-catalyzed dual C-H or N-H functionalization of unfunctionalized indole derivatives with alkenes and arenes [J].

Broggini, Gianluigi ;

Beccalli, Egle M. ;

Fasana, Andrea ;

Gazzola, Silvia .

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2012, 8 :1730-1746

[5] THE TRIKENTRINS - NOVEL INDOLES FROM THE SPONGE TRIKENTRION-FLABELLIFORME [J].

CAPON, RJ ;

MACLEOD, JK ;

SCAMMELLS, PJ .

TETRAHEDRON, 1986, 42 (23) :6545-6550

[6] Rh-Catalyzed Intermolecular Carbenoid Functionalization of Aromatic C-H Bonds by α-Diazomalonates [J].

Chan, Wai-Wing ;

Lo, Siu-Fung ;

Zhou, Zhongyuan ;

Yu, Wing-Yiu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (33) :13565-13568

[7] Ru3(CO)12-catalyzed C-H/CO/olefin coupling of N-pyridylindolines.: Direct carbonylation at a C-H bond δ to the pyridine nitrogen [J].

Chatani, N ;

Yorimitsu, S ;

Asaumi, T ;

Kakiuchi, F ;

Murai, S .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (21) :7557-7560

[8] Recent advances in the transition metal-catalyzed twofold oxidative C-H bond activation strategy for C-C and C-N bond formation [J].

Cho, Seung Hwan ;

Kim, Ji Young ;

Kwak, Jaesung ;

Chang, Sukbok .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :5068-5083

[9] Direct Ortho Arylation of 9-(Pyridin-2-yl)-9H-carbazoles Bearing a Removable Directing Group via Palladium(II)-Catalyzed C-H Bond Activation [J].

Chu, Jean-Ho ;

Wu, Chung-Chiu ;

Chang, Deng-Hsiang ;

Lee, Ya-Ming ;

Wu, Ming-Jung .

ORGANOMETALLICS, 2013, 32 (01) :272-282

[10] Rhodium Catalyzed Chelation-Assisted C-H Bond Functionalization Reactions [J].

Colby, Denise A. ;

Tsai, Andy S. ;

Bergman, Robert G. ;

Ellman, Jonathan A. .

ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) :814-825

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