Sulfur(IV)-Mediated Unsymmetrical Heterocycle Cross-Couplings

Min Zhou, Jet Tsien, Tian Qin

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

Despite the tremendous utilities of metal-mediated cross-couplings in modern organic chemistry, coupling reactions involving nitrogenous heteroarenes remain a challenging undertaking – coordination of Lewis basic atoms into metal centers often necessitate elevated temperature, high catalyst loading, etc. Herein, we report a sulfur (IV) mediated cross-coupling amendable for the efficient synthesis of heteroaromatic substrates. Addition of heteroaryl nucleophiles to a simple, readily-accessible alkyl sulfinyl (IV) chloride allows formation of a trigonal bipyramidal sulfurane intermediate. Reductive elimination therefrom provides bis-heteroaryl products in a practical and efficient fashion.

Original languageEnglish (US)
Pages (from-to)7372-7376
Number of pages5
JournalAngewandte Chemie - International Edition
Volume59
Issue number19
DOIs
StatePublished - May 4 2020

Keywords

  • cross-coupling
  • heterocycles
  • sulfur
  • sulfurane

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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