Catalytic asymmetric C-H insertions of rhodium(II) azavinyl carbenes

Abstract

A highly efficient enantioselective C-H insertion of azavinyl carbenes into unactivated alkanes has been developed. These transition metal carbenes are directly generated from readily available and stable 1-sulfonyl-1,2,3-triazoles in the presence of chiral Rh(II) carboxylates and are used for C-H functionalization of alkanes to access a variety of β-chiral sulfonamides.

Original language	English
Pages (from-to)	10352-10355
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	133
Issue number	27
DOIs	https://doi.org/10.1021/ja202969z
Publication status	Published - 13 Jul 2011
Externally published	Yes

ASJC Scopus subject areas

Chemistry(all)
Catalysis
Biochemistry
Colloid and Surface Chemistry

Access to Document

10.1021/ja202969z

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title = "Catalytic asymmetric C-H insertions of rhodium(II) azavinyl carbenes",

abstract = "A highly efficient enantioselective C-H insertion of azavinyl carbenes into unactivated alkanes has been developed. These transition metal carbenes are directly generated from readily available and stable 1-sulfonyl-1,2,3-triazoles in the presence of chiral Rh(II) carboxylates and are used for C-H functionalization of alkanes to access a variety of β-chiral sulfonamides.",

author = "Stepan Chuprakov and Malik, {Jamal A.} and Mikhail Zibinsky and Fokin, {Valery V.}",

year = "2011",

month = jul,

day = "13",

doi = "10.1021/ja202969z",

language = "English",

volume = "133",

pages = "10352--10355",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

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T1 - Catalytic asymmetric C-H insertions of rhodium(II) azavinyl carbenes

AU - Chuprakov, Stepan

AU - Malik, Jamal A.

AU - Zibinsky, Mikhail

AU - Fokin, Valery V.

PY - 2011/7/13

Y1 - 2011/7/13

N2 - A highly efficient enantioselective C-H insertion of azavinyl carbenes into unactivated alkanes has been developed. These transition metal carbenes are directly generated from readily available and stable 1-sulfonyl-1,2,3-triazoles in the presence of chiral Rh(II) carboxylates and are used for C-H functionalization of alkanes to access a variety of β-chiral sulfonamides.

AB - A highly efficient enantioselective C-H insertion of azavinyl carbenes into unactivated alkanes has been developed. These transition metal carbenes are directly generated from readily available and stable 1-sulfonyl-1,2,3-triazoles in the presence of chiral Rh(II) carboxylates and are used for C-H functionalization of alkanes to access a variety of β-chiral sulfonamides.

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