Ruthenium Catalyzed Directing Group-Free C2-Selective Carbenoid Functionalization of Indoles by α-Aryldiazoesters

被引：113

作者：

Chan, Wai-Wing

Yeung, Shing-Hin

Zhou, Zhongyuan

Chan, Albert S. C.

Yu, Wing-Yiu ^{[1
]}

机构：

[1] Hong Kong Polytech Univ, Open Lab Chirotechnol, Inst Mol Technol Drug Discovery & Synth, Kowloon, Hong Kong, Peoples R China

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 03期

关键词：

C-H BOND; FRIEDEL-CRAFTS ALKYLATIONS; INTRAMOLECULAR CYCLOPROPANATION; ARYLATION; INSERTION; DECOMPOSITION; HETEROCYCLES; DIAZOESTERS; ACTIVATION; COMPLEXES;

D O I：

10.1021/ol9028226

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A directing group-free approach for C2-selective carbenoid functionalization of NH-indoles is presented. Using [RuCl2(p-cymene)](2) as catalyst and alpha-aryldiazoesters as carbenoid source, 2-alkylated indoles were obtained in up to 96% isolated yield. Similarly, a regioselective carbenoid functionalization of NH-pyrroles was also achieved.

引用

页码：604 / 607

页数：4

共 55 条

[11] Catalytic asymmetric C-H activation of alkanes and tetrahydrofuran
Davies, HML
Hansen, T
Churchill, MR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (13) : 3063 - 3070
[12] Catalytic enantioselective C-H activation by means of metal-carbenoid-induced C-H insertion
Davies, HML
Beckwith, REJ
[J]. CHEMICAL REVIEWS, 2003, 103 (08) : 2861 - 2903
[13] Asymmetric intramolecular C-H insertions of aryldiazoacetates
Davies, HML
Grazini, MVA
Aouad, E
[J]. ORGANIC LETTERS, 2001, 3 (10) : 1475 - 1477
[14] Catalytic C-H functionalization by metal carbenoid and nitrenoid insertion
Davies, Huw M. L.
Manning, James R.
[J]. NATURE, 2008, 451 (7177) : 417 - 424
[15] RHODIUM(II) CARBOXYLATE-CATALYZED REACTIONS OF DIAZOESTERS - EVIDENCE FOR AN EQUILIBRIUM BETWEEN FREE CARBENE AND A METAL-CARBENE COMPLEX
DEMONCEAU, A
NOELS, AF
COSTA, JL
HUBERT, AJ
[J]. JOURNAL OF MOLECULAR CATALYSIS, 1990, 58 (01): : 21 - 26
[16] Ruthenium-catalyzed one-pot carbenoid N-H insertion reactions and diastereoselective synthesis of prolines
Deng, Qing-Hai
Xu, Hai-Wei
Yuen, Angella Wing-Hoi
Xu, Zhen-Jiang
Che, Chi-Ming
[J]. ORGANIC LETTERS, 2008, 10 (08) : 1529 - 1532
[17] Asymmetric friedel-crafts alkylations of indoles with ethyl glyoxylate catalyzed by (S)-BINOL-titanium(IV) complex: Direct access to enantiomerically enriched 3-indolyl(hydroxy) acetates
Dong, Hong-Ming
Lu, Hai-Hua
Lu, Liang-Qiu
Chen, Cai-Bao
Xiao, Wen-Jing
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (10) : 1597 - 1603
[18] Doyle M. P., 1998, MODERN CATALYTIC MET
[19] Doyle M.P., CHEM REV ASAP ARTICL, DOI [DOI 10.1021/CR900239N, 10.1021/cr900239n.]
[20] Comparative enantiocontrol with allyl phenyldiazoacetates in asymmetric catalytic intramolecular cyclopropanation
Doyle, MP
Hu, WH
Weathers, TM
[J]. CHIRALITY, 2003, 15 (04) : 369 - 373

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