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

Min Zhou, Jet Tsien, Tian Qin

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

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)
Pages (from-to)1962-1966
Number of pages5
JournalSynlett
Volume31
Issue number20
DOIs
StatePublished - Dec 17 2020

Keywords

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

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Unsymmetrical Heterocycle Cross-Couplings Enabled by Sulfur(IV) Reagents'. Together they form a unique fingerprint.

Cite this