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

研究成果: Article査読

106 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)2643-2655
ページ数13
ジャーナルAdvanced Synthesis and Catalysis
352
14-15
DOI
出版ステータスPublished - 2010 10月 4

ASJC Scopus subject areas

  • 触媒
  • 有機化学

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