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

被引：4
|
作者：
Murata, Yuki [1 ]
Terazoe, Aki [1 ]
Kiba, Misato [1 ]
Kitamura, Yuki [1 ]
Matsumura, Mio [1 ]
Yasuike, Shuji [1 ]
机构：
[1] Aichi Gakuin Univ, Sch Pharmaceut Sci, Chikusa Ku, 1-100 Kusumoto Cho, Nagoya, Aichi 4648650, Japan
来源：
TETRAHEDRON LETTERS | 2020年 / 61卷 / 30期
关键词：
Bismuth; Cross-coupling reaction; Palladium catalyst; Thiazole; Triarylbismuthine; CARBON-CARBON; BORONIC ACIDS; CYCLIC THIOAMIDES; BOND FORMATION; PALLADIUM; REAGENTS; ARYLATION;
D O I：
10.1016/j.tetlet.2020.152152
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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 degrees 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. (C) 2020 Elsevier Ltd. All rights reserved.
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页数：4
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