Liebeskind-Srogl-type cross-coupling reaction of azole-2-thiones with triarylbismuthines: Synthesis of 2-arylazoles

Yuki Murata, Aki Terazoe, Misato Kiba, Yuki Kitamura, Mio Matsumura, Shuji Yasuike

doi:10.1016/j.tetlet.2020.152152

Liebeskind-Srogl-type cross-coupling reaction of azole-2-thiones with triarylbismuthines: Synthesis of 2-arylazoles

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書誌事項

公開日: 2020-07

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DOI

10.1016/j.tetlet.2020.152152

公開者: Elsevier BV

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説明

Abstract Liebeskind-Srogl-type C(HetAr)–C(Ar) bond formation using trivalent organobismuth compounds as a new class of arylating reagents is described. The reaction of benzazole-2-thiones with triarylbismuthines in the presence of 10 mol% Pd(dba)2 and 2.0 equiv. Cu(OAc)2 at 80 °C affords 2-arylbenzothiazoles, benzoxazoles, and N-methyl benzimidazole in moderate-to-high yield. The reaction is sensitive to the electronic nature of triarylbismuthines: compounds bearing an electron-withdrawing group on the phenyl ring showed higher reactivity than those having an electron-donating group.