1609585-04-7Relevant articles and documents
N-heterocyclic carbene catalyzed umpolung of styrenes: Mechanistic elucidation and selective tail-to-tail dimerization
Schedler, Michael,Wurz, Nathalie E.,Daniliuc, Constantin G.,Glorius, Frank
, p. 3134 - 3137 (2014)
The reaction between N-heterocyclic carbenes (NHCs) and styrenes yields alkyl-substituted azolium salts, which are able to form nucleophilic deoxy Breslow intermediates by simple deprotonation. This hitherto unknown reaction of NHCs represents a new way to generate deoxy Breslow intermediates and paves the way for the selective NHC-catalyzed tail-to-tail homodimerization of styrenes. This reaction significantly broadens the scope of the Michael umpolung and provides a new method to generate 1,4-diaryl compounds.
