Use of molecular oxygen as a reoxidant in the synthesis of 2-substituted benzothiazoles via palladium-catalyzed C-H functionalization/intramolecular C-S bond formation

Kiyofumi Inamoto, Chisa Hasegawa, Junpei Kawasaki, Kou Hiroya, Takayuki Doi

Research output: Contribution to journalArticle

91 Citations (Scopus)

Abstract

Molecular oxygen (O2) was successfully employed as a reoxidant in cyclizations of thiobenzanilides 1a-s through a palladium-catalyzed C-H functionalization/intramolecular C-S bond formation process, leading to an efficient, green method for the synthesis of 2-arylbenzothiazoles 2a-s. Addition of cesium fluoride (CsF) greatly enhanced the reactions, which produced variously substituted 2-arylbenzothiazoles with good functional group tolerance. Thioureas 4a-j were also found to be suitable substrates for the cyclization process using a palladium/O2 catalyst system, thus generating 2-aminobenzothiazoles 5a-j. One-pot syntheses of 2-aminobenzothiazoles 5a-j from aryl isothiocyanates 6 and amines 7 were also successful.

Original languageEnglish
Pages (from-to)2643-2655
Number of pages13
JournalAdvanced Synthesis and Catalysis
Volume352
Issue number14-15
DOIs
Publication statusPublished - 2010 Oct 4

Keywords

  • C-H functionalization
  • C-S bond formation
  • benzothiazoles
  • cyclization
  • molecular oxygen
  • palladium

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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