Ruthenium catalyzed directing group-free C2-selective carbenoid functionalization of indoles by α-aryldiazoesters

Wai Wing Chan; Shing Hin Yeung; Zhongyuan Zhou; Albert S.C. Chan; Wing Yiu Yu

doi:10.1021/ol9028226

Ruthenium catalyzed directing group-free C2-selective carbenoid functionalization of indoles by α-aryldiazoesters

Wai Wing Chan, Shing Hin Yeung, Zhongyuan Zhou, Albert S.C. Chan, Wing Yiu Yu

Research output: Journal article publication › Journal article › Academic research › peer-review

90 Citations (Scopus)

Abstract

[Chemical equation presented] A directing group-free approach for C2-selective carbenoid functionalization of NH-indoles is presented. Using [RuCl2(p-cymene)]2as catalyst and α-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.

Original language	English
Pages (from-to)	604-607
Number of pages	4
Journal	Organic Letters
Volume	12
Issue number	3
DOIs	https://doi.org/10.1021/ol9028226
Publication status	Published - 5 Feb 2010

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

More information

10.1021/ol9028226

Scopus Link

Cite this

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title = "Ruthenium catalyzed directing group-free C2-selective carbenoid functionalization of indoles by α-aryldiazoesters",

abstract = "[Chemical equation presented] A directing group-free approach for C2-selective carbenoid functionalization of NH-indoles is presented. Using [RuCl2(p-cymene)]2as catalyst and α-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.",

author = "Chan, {Wai Wing} and Yeung, {Shing Hin} and Zhongyuan Zhou and Chan, {Albert S.C.} and Yu, {Wing Yiu}",

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AU - Chan, Wai Wing

AU - Yeung, Shing Hin

AU - Zhou, Zhongyuan

AU - Chan, Albert S.C.

AU - Yu, Wing Yiu

PY - 2010/2/5

Y1 - 2010/2/5

N2 - [Chemical equation presented] A directing group-free approach for C2-selective carbenoid functionalization of NH-indoles is presented. Using [RuCl2(p-cymene)]2as catalyst and α-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.

AB - [Chemical equation presented] A directing group-free approach for C2-selective carbenoid functionalization of NH-indoles is presented. Using [RuCl2(p-cymene)]2as catalyst and α-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.

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