Transition Metal-Catalyzed Cascade Cyclization of Aryldiynes to Halogenated Benzo[b]naphtho[2,1-d]thiophene Derivatives
Transition Metal-Catalyzed Cascade Cyclization of Aryldiynes to Halogenated Benzo[b]naphtho[2,1-d]thiophene Derivatives
复制标题
DOI：
10.1021/jo500377v
复制
发表时间：
2014-05-16
影响因子：
3.6
通讯作者：
Wu, Ming-Jung
中科院分区：
文献类型：
--
作者：
Chen, Chin-Chau;Chen, Chu-Mei;Wu, Ming-Jung
2-(2-(2-(2-取代乙炔)苯基)乙炔)硫代苯甲醚(1)与5mol%的Ph3PAuCl/AgSbF6和2当量的NiS在CH2Cl2中回流反应，得到高产率的碘取代苯并[b]萘并[2，1-d]噻吩环化合物(6)。化合物1在回流四氢呋喃中加入5%的PdX2和3当量的CuX2，也得到了氯代和溴代苯并[b]萘并[2，1-d]噻吩衍生物(8和9)。
Treatment of 2-(2-(2-(2-substituted ethynyl)phenyl)ethynyl)thioanisoles (1) with 5 mol % of Ph3PAuCl/AgSbF6 and 2 equiv of NIS at refluxing CH2Cl2 gave iodo-substituted benzo[b]naphtho[2,1-d]thiophene (6) in good yields. Chloro- and bromo-substituted benzo [b]naphtho [2,1-d] thiophene derivatives (8 and 9) were also generated by treating compound 1 with 5 mol % of PdX2 and 3 equiv of CuX2 at refluxing THF.