CAJ | 학술논문

芳香族的溴化物在钯催化剂和六丁基二锡存在下经过均同偶联反应能生成二联芳烃.该合成方法在微波协助下只需15 min便可得到60%~84%的得率,具有方便、快捷、普适等特点.各种缺电子和富电子芳烃和杂环溴化物,如苯、噻吩、呋喃、吡啶、噻唑和嘧啶的溴化物均易偶联.此方法还适应于稠环芳烃如萘、喹啉、苯并噻吩和吲哚的溴化物,且与羟基、氨基、羧基、醛基、酰基、酯基、硝基、氰基等反应性基团相容.反应是先通过溴代芳烃与六丁基二锡原位生成芳烃有机锡,芳烃有机锡再与溴代芳烃发生Stille偶联反应进行的.
방향족적추화물재파최화제화륙정기이석존재하경과균동우련반응능생성이련방경.해합성방법재미파협조하지수15 min편가득도60%~84%적득솔,구유방편、쾌첩、보괄등특점.각충결전자화부전자방경화잡배추화물,여분、새분、부남、필정、새서화밀정적추화물균역우련.차방법환괄응우주배방경여내、규람、분병새분화신타적추화물,차여간기、안기、최기、철기、선기、지기、초기、청기등반응성기단상용.반응시선통과추대방경여륙정기이석원위생성방경유궤석,방경유궤석재여추대방경발생Stille우련반응진행적.
Biaryls and bis-heterocycles can be synthesized conveniently, efficiently, and generally via palladium(0)-catalyzed homocoupling of aryl bromides with hexabutylditin as reductant. This method delivers biaryls in good to excellent yields in 15 min under controlled microwave irradiation. Various bromo-derivatives of electron-rich or electron-poor arenes and aromatic heterocycles including benzene, thiophene, furan, pyridine, thiazole, and pyrimidine are easily coupled. This homocoupling method is also applicable to the bromides of fused-ring arenes such as naphthalene, quinoline, benzothiophene, and indole. The procedure is compatible with various reactive functionalities such as hydroxy, amino, carboxyl, formyl, acyl, alkoxycarbonyl, nitro, and cyano groups. The reaction appears to proceed through in situ formation of an aryl tin, followed by a Stille coupling to the aryl bromide.