A novel palladium-mediated coupling approach to 2,3-disubstituted benzo[b]thiophenes and its application to the synthesis of tubulin binding agents
A novel palladium-mediated coupling approach to 2,3-disubstituted benzo[b]thiophenes and its application to the synthesis of tubulin binding agents
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DOI：
10.1021/ol0067179
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发表时间：
2001-03-08
期刊：
影响因子：
5.2
通讯作者：
Hamel, E
中科院分区：
文献类型：
--
作者：
Flynn, BL;Verdier-Pinard, P;Hamel, E
[图表]灵活的，收敛的2，3-二取代苯并[B]噻吩的方法已经开发出来。最简洁的方法是邻溴碘代苯与苄基乙炔和乙炔锌依次偶联得到苄基邻乙炔基苯硫醚，再与碘反应得到3-碘代苯并[B]噻吩，经5-内二碘环化得到3-碘代苯并[B]噻吩。这些碘化物可以使用钯介导的偶联和/或金属化技术进一步加工。该方法已应用于一些新型微管蛋白结合剂的合成。
[GRAPHICS]Flexible, convergent access to 2,3-disubstituted benzo[b]thiophenes has been developed. The most concise approach involves sequential coupling of o-bromoiodobenzenes with benzylmercaptan and zinc acetylides to give benzyl o-ethynylphenyl sulfides which react with iodine to give 3-iodobenzo[b]thiophenes in a 5-endo-dig iodocyclization. These iodides can be further elaborated using palladium-mediated coupling and/or metalation techniques. This method has been applied to the synthesis of some novel tubulin binding agents.