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

Stepan Chuprakov, Jamal A. Malik, Mikhail Zibinsky, Valery V. Fokin

Research output: Contribution to journal › Article

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

Fingerprint

Rhodium

Alkanes

Paraffins

Sulfonamides

Transition metals

Metals

carbene

1-sulfonyl-1,2,3-triazole

ASJC Scopus subject areas

Chemistry(all)
Catalysis
Biochemistry
Colloid and Surface Chemistry

Cite this

Chuprakov, S., Malik, J. A., Zibinsky, M., & Fokin, V. V. (2011). Catalytic asymmetric C-H insertions of rhodium(II) azavinyl carbenes. Journal of the American Chemical Society, 133(27), 10352-10355. https://doi.org/10.1021/ja202969z

Catalytic asymmetric C-H insertions of rhodium(II) azavinyl carbenes. / Chuprakov, Stepan; Malik, Jamal A.; Zibinsky, Mikhail; Fokin, Valery V.

In: Journal of the American Chemical Society, Vol. 133, No. 27, 13.07.2011, p. 10352-10355.

Research output: Contribution to journal › Article

Chuprakov, S, Malik, JA, Zibinsky, M & Fokin, VV 2011, 'Catalytic asymmetric C-H insertions of rhodium(II) azavinyl carbenes', Journal of the American Chemical Society, vol. 133, no. 27, pp. 10352-10355. https://doi.org/10.1021/ja202969z

Chuprakov S, Malik JA, Zibinsky M, Fokin VV. Catalytic asymmetric C-H insertions of rhodium(II) azavinyl carbenes. Journal of the American Chemical Society. 2011 Jul 13;133(27):10352-10355. https://doi.org/10.1021/ja202969z

Chuprakov, Stepan ; Malik, Jamal A. ; Zibinsky, Mikhail ; Fokin, Valery V. / Catalytic asymmetric C-H insertions of rhodium(II) azavinyl carbenes. In: Journal of the American Chemical Society. 2011 ; Vol. 133, No. 27. pp. 10352-10355.

@article{4876ccf251724623b7ed4cbb55591fa3,

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 = "7",

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",

number = "27",

}

TY - JOUR

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.

UR - http://www.scopus.com/inward/record.url?scp=79960049239&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=79960049239&partnerID=8YFLogxK

U2 - 10.1021/ja202969z

DO - 10.1021/ja202969z

M3 - Article

VL - 133

SP - 10352

EP - 10355

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 27

ER -

Access to Document

10.1021/ja202969z