Unsymmetrical Heterocycle Cross-Couplings Enabled by Sulfur(IV) Reagents

Min Zhou, Jet Tsien, Tian Qin

Research output: Contribution to journalArticlepeer-review

Abstract

Whereas metal-mediated cross-couplings find broad applications in syntheses of medicines, agrochemicals, and natural products, these powerful transformations have limited utility for Lewis basic substrates (e.g., heteroarenes), wherein basic functionalities coordinate to the metal center, hindering product formation. In this context, we have developed a transition-metal-free cross-coupling reaction mediated by sulfur(IV). This method leverages the ability of simple alkyl sulfinyl(IV) chlorides to form bipyramidal sulfurane complexes to drive a pseudo 'reductive elimination' process from the hypervalent sulfur atom, thereby readily providing unsymmetrical biheteroarenes. 1 Introduction 2 Historical Sulfurane(IV)-Mediated Couplings 3 Unsymmetrical Heterocycle Cross-Couplings 4 Conclusion.

Original languageEnglish (US)
JournalSynlett
DOIs
StateAccepted/In press - 2020

Keywords

  • cross-coupling
  • Grignard reagents
  • sulfur coupling
  • sulfuranes
  • unsymmetrical biheteroarenes

ASJC Scopus subject areas

  • Organic Chemistry

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