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

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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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Publication details

The article was received on 23 Aug 2017, accepted on 13 Sep 2017 and first published on 14 Sep 2017


Article type: Research Article
DOI: 10.1039/C7QO00750G
Citation: Org. Chem. Front., 2017, Advance Article
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    Ultra-fast Suzuki and Heck reactions for the synthesis of styrenes and stilbenes using arenediazonium salts as super-electrophiles

    M. E. Trusova, M. Rodriguez-Zubiri, K. V. Kutonova, N. Jung, S. Bräse, F. Felpin and P. S. Postnikov, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C7QO00750G

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