Suzuki-Miyaura synthesis of m-terphenyl thioethers and their facilitated oxidation caused by through-space π···S···π interaction

Takuhei Yamamoto, Malika Ammam, Sue A. Roberts, George S. Wilson, Richard S. Glass

Research output: Contribution to journalArticle

4 Scopus citations

Abstract

S-tert-Butyl m-terphenyl thioethers have been efficiently synthesized by Suzuki-Miyaura coupling reactions with 2,6-dibromo-S-tert-butylthio benzene. Selective monocoupling could be achieved with o-substituted boronic acids. This facilitated the synthesis of unsymmetrical S-tert-butyl m-terphenyl thioethers and bis(S-tert-butyl m-terphenyl thioether)s. The study of their electrochemistry showed facilitated oxidations resulting from through-space π···S···π interactions.

Original languageEnglish (US)
Pages (from-to)2527-2534
Number of pages8
JournalTetrahedron
Volume72
Issue number20
DOIs
StatePublished - May 19 2016

Keywords

  • Electrochemistry
  • Regioselectivity
  • Unsymmetrical substitution

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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