Organic Chemistry Portal



Stereoselective 1,3-Insertions of Rhodium(II) Azavinyl Carbenes

Stepan Chuprakov, Brady T. Worrell, Nicklas Selander, Rakesh K. Sit and Valery V. Fokin*

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

S. Chuprakov, B. T. Worrell, N. Selander, R. K. Sit, V. V. Fokin, J. Am. Chem. Soc., 2014, 136, 195-202.

DOI: 10.1021/ja408185c

see article for more reactions


Rhodium(II) azavinyl carbenes, which are conveniently generated from 1-sulfonyl-1,2,3-triazoles, undergo a facile, mild, and convergent formal 1,3-insertion into N-H and O-H bonds of primary and secondary amides, various alcohols, and carboxylic acids to afford a wide range of vicinally bisfunctionalized (Z)-olefins with perfect regio- and stereoselectivity.

see article for more examples

Key Words

enamines, sulfonamides, carbamates, amides

ID: J48-Y2014