Gold(I)-Catalyzed Selective Hydroarylation of Indoles with Haloalkynes

Cunbo Wei; Jiawen Wu; Lizhu Zhang; Zhonghua Xia

doi:10.1021/acs.orglett.2c01921

Gold(I)-Catalyzed Selective Hydroarylation of Indoles with Haloalkynes

Cunbo Wei
, Jiawen Wu
, Lizhu Zhang
, Zhonghua Xia^*

^*Corresponding author for this work

School of Material Science and Engineering

Beijing Institute of Technology

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

14 Citations (Scopus)

Abstract

A highly regio- and stereoselective synthesis of a Z-alkenyl indole via the gold-catalyzed addition of an indole to a haloalkyne was developed. In the presence of gold catalyst SIPrAuCl and cocatalyst NaBARF, a broad range of indoles react with haloalkynes to afford Z-alkenyl indoles with high selectivity at room temperature. Computational studies suggest that the hydroarylation reaction takes place via a concerted C2 addition pathway of the indole to the activated haloalkyne. 2022 American Chemical Society.

Original language	English
Pages (from-to)	4689-4693
Number of pages	5
Journal	Organic Letters
Volume	24
Issue number	25
DOIs	https://doi.org/10.1021/acs.orglett.2c01921
Publication status	Published - 1 Jul 2022

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title = "Gold(I)-Catalyzed Selective Hydroarylation of Indoles with Haloalkynes",

abstract = "A highly regio- and stereoselective synthesis of a Z-alkenyl indole via the gold-catalyzed addition of an indole to a haloalkyne was developed. In the presence of gold catalyst SIPrAuCl and cocatalyst NaBARF, a broad range of indoles react with haloalkynes to afford Z-alkenyl indoles with high selectivity at room temperature. Computational studies suggest that the hydroarylation reaction takes place via a concerted C2 addition pathway of the indole to the activated haloalkyne. 2022 American Chemical Society.",

author = "Cunbo Wei and Jiawen Wu and Lizhu Zhang and Zhonghua Xia",

year = "2022",

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doi = "10.1021/acs.orglett.2c01921",

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TY - JOUR

T1 - Gold(I)-Catalyzed Selective Hydroarylation of Indoles with Haloalkynes

AU - Wei, Cunbo

AU - Wu, Jiawen

AU - Zhang, Lizhu

AU - Xia, Zhonghua

PY - 2022/7/1

Y1 - 2022/7/1

N2 - A highly regio- and stereoselective synthesis of a Z-alkenyl indole via the gold-catalyzed addition of an indole to a haloalkyne was developed. In the presence of gold catalyst SIPrAuCl and cocatalyst NaBARF, a broad range of indoles react with haloalkynes to afford Z-alkenyl indoles with high selectivity at room temperature. Computational studies suggest that the hydroarylation reaction takes place via a concerted C2 addition pathway of the indole to the activated haloalkyne. 2022 American Chemical Society.

AB - A highly regio- and stereoselective synthesis of a Z-alkenyl indole via the gold-catalyzed addition of an indole to a haloalkyne was developed. In the presence of gold catalyst SIPrAuCl and cocatalyst NaBARF, a broad range of indoles react with haloalkynes to afford Z-alkenyl indoles with high selectivity at room temperature. Computational studies suggest that the hydroarylation reaction takes place via a concerted C2 addition pathway of the indole to the activated haloalkyne. 2022 American Chemical Society.

UR - https://www.scopus.com/pages/publications/85133960093

U2 - 10.1021/acs.orglett.2c01921

DO - 10.1021/acs.orglett.2c01921

M3 - Article

C2 - 35714368

AN - SCOPUS:85133960093

SN - 1523-7060

VL - 24

SP - 4689

EP - 4693

JO - Organic Letters

JF - Organic Letters

IS - 25

ER -

Gold(I)-Catalyzed Selective Hydroarylation of Indoles with Haloalkynes

Abstract

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