Unusual (Z)-selective palladium(II)-catalysed addition of aryl boronic acids to vinylaziridines

Authors

Jiexiang Yin, University of WollongongFollow
Theresa Mekelburg, University of WollongongFollow
Christopher J. T Hyland, University of WollongongFollow

RIS ID

95134

Publication Details

Yin, J., Mekelburg, T. & Hyland, C. (2014). Unusual (Z)-selective palladium(II)-catalysed addition of aryl boronic acids to vinylaziridines. Organic and Biomolecular Chemistry, 12 (45), 9113-9115.

Abstract

The palladium(II)-catalysed addition of arylboronic acids to vinylaziridines has been developed. This reaction proceeds via an insertion/ring-opening process to provide (Z)-allylsulfonamides preferentially. This stereoselectivity is complimentary to existing methods that typically proceed via a SN2′ mechanism to yield (E)-allylsulfonamides. Electron-deficient arylboronic acids were the optimum substrates for this reaction, while electron-donating groups on the aromatic ring of the boronic acids resulted in moderate yields.