Arylation of rhodium(II) azavinyl carbenes with boronic acids

Abstract

A highly efficient and stereoselective arylation of in situ-generated azavinyl carbenes affording 2,2-diaryl enamines at ambient temperatures has been developed. These transition-metal carbenes are directly produced from readily available and stable 1-sulfonyl-1,2,3-triazoles in the presence of a rhodium carboxylate catalyst. In several cases, the enamines generated in this reaction can be cyclized into substituted indoles employing copper catalysis.

Original language	English
Pages (from-to)	14670-14673
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	134
Issue number	36
DOIs	https://doi.org/10.1021/ja3062453
Publication status	Published - 12 Sep 2012
Externally published	Yes

ASJC Scopus subject areas

Chemistry(all)
Catalysis
Biochemistry
Colloid and Surface Chemistry

Access to Document

10.1021/ja3062453

Fingerprint Dive into the research topics of 'Arylation of rhodium(II) azavinyl carbenes with boronic acids'. Together they form a unique fingerprint.

Cite this

@article{e4e29a9b49ea4f50acb1983ebabfe69d,

title = "Arylation of rhodium(II) azavinyl carbenes with boronic acids",

abstract = "A highly efficient and stereoselective arylation of in situ-generated azavinyl carbenes affording 2,2-diaryl enamines at ambient temperatures has been developed. These transition-metal carbenes are directly produced from readily available and stable 1-sulfonyl-1,2,3-triazoles in the presence of a rhodium carboxylate catalyst. In several cases, the enamines generated in this reaction can be cyclized into substituted indoles employing copper catalysis.",

author = "Nicklas Selander and Worrell, {Brady T.} and Stepan Chuprakov and Subash Velaparthi and Fokin, {Valery V.}",

year = "2012",

month = sep,

day = "12",

doi = "10.1021/ja3062453",

language = "English",

volume = "134",

pages = "14670--14673",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "36",

}

TY - JOUR

T1 - Arylation of rhodium(II) azavinyl carbenes with boronic acids

AU - Selander, Nicklas

AU - Worrell, Brady T.

AU - Chuprakov, Stepan

AU - Velaparthi, Subash

AU - Fokin, Valery V.

PY - 2012/9/12

Y1 - 2012/9/12

N2 - A highly efficient and stereoselective arylation of in situ-generated azavinyl carbenes affording 2,2-diaryl enamines at ambient temperatures has been developed. These transition-metal carbenes are directly produced from readily available and stable 1-sulfonyl-1,2,3-triazoles in the presence of a rhodium carboxylate catalyst. In several cases, the enamines generated in this reaction can be cyclized into substituted indoles employing copper catalysis.

AB - A highly efficient and stereoselective arylation of in situ-generated azavinyl carbenes affording 2,2-diaryl enamines at ambient temperatures has been developed. These transition-metal carbenes are directly produced from readily available and stable 1-sulfonyl-1,2,3-triazoles in the presence of a rhodium carboxylate catalyst. In several cases, the enamines generated in this reaction can be cyclized into substituted indoles employing copper catalysis.

UR - http://www.scopus.com/inward/record.url?scp=84866369102&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84866369102&partnerID=8YFLogxK

U2 - 10.1021/ja3062453

DO - 10.1021/ja3062453

M3 - Article

C2 - 22913576

AN - SCOPUS:84866369102

VL - 134

SP - 14670

EP - 14673

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 36

ER -