Organic Chemistry Portal



Catalytic Asymmetric C-H Insertions of Rhodium(II) Azavinyl Carbenes

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

*The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States, Email:

S. Chuprakov, J. A. Malik, M. Zibinsky, V. V. Fokin, J. Am. Chem. Soc., 2011, 133, 10352-10355.

DOI: 10.1021/ja202969z


Transition metal carbenes can directly be generated from readily available and stable 1-sulfonyl-1,2,3-triazoles in the presence of chiral Rh(II) carboxylates and can be used in a highly efficient enantioselective C-H insertion of azavinyl carbenes into unactivated alkanes to access various β-chiral sulfonamides.

see article for more examples

proposed reaction pathway

Key Words

benzylation, amines

ID: J48-Y2011-1850