Issue 45, 2014

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

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.

Graphical abstract: Unusual (Z)-selective palladium(ii)-catalysed addition of aryl boronic acids to vinylaziridines

Supplementary files

Article information

Article type
Communication
Submitted
21 Aug 2014
Accepted
06 Oct 2014
First published
07 Oct 2014

Org. Biomol. Chem., 2014,12, 9113-9115

Author version available

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

J. Yin, T. Mekelburg and C. Hyland, Org. Biomol. Chem., 2014, 12, 9113 DOI: 10.1039/C4OB01786B

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