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Unusual (Z)-selective palladium(II)-catalysed addition of aryl boronic acids to vinylaziridines
JieXiang Yin1, Theresa Mekelburg, Christopher Hyland
1School of Chemistry, University of Wollongong, Wollongong, New South Wales 2522, Australia. chrhyl@uow.edu.au.
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.
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