Selectivity Control in Gold-Catalyzed Hydroarylation of Alkynes with Indoles: Application to Unsymmetrical Bis(indolyl)methanes

Euan B. McLean; Francesca M. Cutolo; Orla J. Cassidy; David J. Burns; Ai-Lan Lee

doi:10.1021/acs.orglett.0c02526

Selectivity Control in Gold-Catalyzed Hydroarylation of Alkynes with Indoles: Application to Unsymmetrical Bis(indolyl)methanes

Euan B. McLean, Francesca M. Cutolo, Orla J. Cassidy, David J. Burns, Ai-Lan Lee

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

28 Citations (Scopus)

40 Downloads (Pure)

Abstract

Gold-catalyzed hydroarylation of unactivated alkynes with indoles have previously been reported to proceed with double indole addition to produce symmetrical bis(indolyl)methanes (BIMs). We demonstrate for the first time that the selectivity of the gold-catalyzed reaction can be fully switched to allow for isolation of the vinylindole products instead. Furthermore, this selective reaction can be utilized to synthesize the more difficult to access unsymmetrical BIMs from readily available starting materials.

Original language	English
Pages (from-to)	6977-6981
Number of pages	5
Journal	Organic letters
Volume	22
Issue number	17
Early online date	26 Aug 2020
DOIs	https://doi.org/10.1021/acs.orglett.0c02526
Publication status	Published - 4 Sept 2020

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/acs.orglett.0c02526

Download pdf
This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.orglett.0c02526
Accepted author manuscript, 456 KB

Cite this

@article{f3742ee38a0043098ddbb99cd47e80f9,

title = "Selectivity Control in Gold-Catalyzed Hydroarylation of Alkynes with Indoles: Application to Unsymmetrical Bis(indolyl)methanes",

abstract = "Gold-catalyzed hydroarylation of unactivated alkynes with indoles have previously been reported to proceed with double indole addition to produce symmetrical bis(indolyl)methanes (BIMs). We demonstrate for the first time that the selectivity of the gold-catalyzed reaction can be fully switched to allow for isolation of the vinylindole products instead. Furthermore, this selective reaction can be utilized to synthesize the more difficult to access unsymmetrical BIMs from readily available starting materials.",

author = "McLean, {Euan B.} and Cutolo, {Francesca M.} and Cassidy, {Orla J.} and Burns, {David J.} and Ai-Lan Lee",

year = "2020",

month = sep,

day = "4",

doi = "10.1021/acs.orglett.0c02526",

language = "English",

volume = "22",

pages = "6977--6981",

journal = "Organic letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "17",

}

TY - JOUR

T1 - Selectivity Control in Gold-Catalyzed Hydroarylation of Alkynes with Indoles

T2 - Application to Unsymmetrical Bis(indolyl)methanes

AU - McLean, Euan B.

AU - Cutolo, Francesca M.

AU - Cassidy, Orla J.

AU - Burns, David J.

AU - Lee, Ai-Lan

PY - 2020/9/4

Y1 - 2020/9/4

N2 - Gold-catalyzed hydroarylation of unactivated alkynes with indoles have previously been reported to proceed with double indole addition to produce symmetrical bis(indolyl)methanes (BIMs). We demonstrate for the first time that the selectivity of the gold-catalyzed reaction can be fully switched to allow for isolation of the vinylindole products instead. Furthermore, this selective reaction can be utilized to synthesize the more difficult to access unsymmetrical BIMs from readily available starting materials.

AB - Gold-catalyzed hydroarylation of unactivated alkynes with indoles have previously been reported to proceed with double indole addition to produce symmetrical bis(indolyl)methanes (BIMs). We demonstrate for the first time that the selectivity of the gold-catalyzed reaction can be fully switched to allow for isolation of the vinylindole products instead. Furthermore, this selective reaction can be utilized to synthesize the more difficult to access unsymmetrical BIMs from readily available starting materials.

UR - http://www.scopus.com/inward/record.url?scp=85090482276&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.0c02526

DO - 10.1021/acs.orglett.0c02526

M3 - Article

C2 - 32845648

SN - 1523-7060

VL - 22

SP - 6977

EP - 6981

JO - Organic letters

JF - Organic letters

IS - 17

ER -

Selectivity Control in Gold-Catalyzed Hydroarylation of Alkynes with Indoles: Application to Unsymmetrical Bis(indolyl)methanes

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint