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

Marina E. Trusova, Mireia Rodriguez-Zubiri, Ksenia V. Kutonova, Nicole Jung, Stefan Bräse, François Xavier Felpin, Pavel S. Postnikov

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)

Abstract

The super-electrophilic properties of arenediazonium salts have been exploited for achieving ultra-fast palladium-catalyzed coupling reactions with turnover frequencies up to 16200 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.

Original languageEnglish
Pages (from-to)41-45
Number of pages5
JournalOrganic Chemistry Frontiers
Volume5
Issue number1
DOIs
Publication statusPublished - 1 Jan 2018

ASJC Scopus subject areas

  • Organic Chemistry

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