General and efficient synthesis of indoles through triazene-directed c-h annulation

Chengming Wang; Huan Sun; Yan Fang; Yong Huang

doi:10.1002/anie.201301742

General and efficient synthesis of indoles through triazene-directed c-h annulation

Chengming Wang, Huan Sun, Yan Fang, Yong Huang

Research output: Contribution to journal › Journal Article › peer-review

229 Citations (Scopus)

Abstract

Unprotected indoles are prepared with the title method, which has a wide scope for alkynes. Excellent regioselectivity was accomplished for aryl-alkyl and alkyl-alkyl disubstituted acetylenes. This reaction features an unusual 1,2 rhodium migration and ring-contraction-triggered N-N bond cleavage. It allows rapid conversion of the reaction products into several functional molecules.

Original language	English
Pages (from-to)	5795-5798
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	52
Issue number	22
DOIs	https://doi.org/10.1002/anie.201301742
Publication status	Published - 27 May 2013
Externally published	Yes

Keywords

C-H activation
N-N cleavage
indole
rhodium
triazene

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10.1002/anie.201301742

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abstract = "Unprotected indoles are prepared with the title method, which has a wide scope for alkynes. Excellent regioselectivity was accomplished for aryl-alkyl and alkyl-alkyl disubstituted acetylenes. This reaction features an unusual 1,2 rhodium migration and ring-contraction-triggered N-N bond cleavage. It allows rapid conversion of the reaction products into several functional molecules.",

keywords = "C-H activation, N-N cleavage, indole, rhodium, triazene",

author = "Chengming Wang and Huan Sun and Yan Fang and Yong Huang",

year = "2013",

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T1 - General and efficient synthesis of indoles through triazene-directed c-h annulation

AU - Wang, Chengming

AU - Sun, Huan

AU - Fang, Yan

AU - Huang, Yong

PY - 2013/5/27

Y1 - 2013/5/27

N2 - Unprotected indoles are prepared with the title method, which has a wide scope for alkynes. Excellent regioselectivity was accomplished for aryl-alkyl and alkyl-alkyl disubstituted acetylenes. This reaction features an unusual 1,2 rhodium migration and ring-contraction-triggered N-N bond cleavage. It allows rapid conversion of the reaction products into several functional molecules.

AB - Unprotected indoles are prepared with the title method, which has a wide scope for alkynes. Excellent regioselectivity was accomplished for aryl-alkyl and alkyl-alkyl disubstituted acetylenes. This reaction features an unusual 1,2 rhodium migration and ring-contraction-triggered N-N bond cleavage. It allows rapid conversion of the reaction products into several functional molecules.

KW - C-H activation

KW - N-N cleavage

KW - indole

KW - rhodium

KW - triazene

UR - https://www.webofscience.com/wos/woscc/full-record/WOS:000319741100021

UR - https://openalex.org/W2139520643

UR - https://www.scopus.com/pages/publications/84878047362

U2 - 10.1002/anie.201301742

DO - 10.1002/anie.201301742

M3 - Journal Article

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SN - 1433-7851

VL - 52

SP - 5795

EP - 5798

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 22

ER -

General and efficient synthesis of indoles through triazene-directed c-h annulation

Abstract

Keywords

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