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 journalArticle

5 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

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Styrenes
Stilbenes
Salts
Palladium
Functional groups
Polymerization
potassium vinyltrifluoroborate

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Ultra-fast Suzuki and Heck reactions for the synthesis of styrenes and stilbenes using arenediazonium salts as super-electrophiles. / Trusova, Marina E.; Rodriguez-Zubiri, Mireia; Kutonova, Ksenia V.; Jung, Nicole; Bräse, Stefan; Felpin, François Xavier; Postnikov, Pavel S.

In: Organic Chemistry Frontiers, Vol. 5, No. 1, 01.01.2018, p. 41-45.

Research output: Contribution to journalArticle

Trusova, Marina E. ; Rodriguez-Zubiri, Mireia ; Kutonova, Ksenia V. ; Jung, Nicole ; Bräse, Stefan ; Felpin, François Xavier ; Postnikov, Pavel S. / Ultra-fast Suzuki and Heck reactions for the synthesis of styrenes and stilbenes using arenediazonium salts as super-electrophiles. In: Organic Chemistry Frontiers. 2018 ; Vol. 5, No. 1. pp. 41-45.
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