Ultra-fast Suzuki and Heck reactions for the synthesis of styrenes and stilbenes using arenediazonium salts as super-electrophiles?

Organic Chemistry Frontiers Pub Date: 2017-09-14 DOI: 10.1039/C7QO00750G

Abstract

The super-electrophilic properties of arenediazonium salts have been exploited for achieving ultra-fast palladium-catalyzed coupling reactions with turnover frequencies up to 16?200 h?1. These ultra-fast coupling reactions have been exemplified with the synthesis of prone-to-polymerization styrenes within seconds through Suzuki cross-couplings with potassium vinyltrifluoroborate. Heterocycles and functional groups such as halides were well tolerated. The ambivalent properties of potassium vinyltrifluoroborate also allowed the development of ultra-fast sequential Suzuki–Heck reactions for the preparation of symmetrical and unsymmetrical stilbenes within minutes.

Graphical abstract: Ultra-fast Suzuki and Heck reactions for the synthesis of styrenes and stilbenes using arenediazonium salts as super-electrophiles
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