Palladium-Catalyzed Synthesis of Benzothiophenes via Cross-Dehydrogenative Coupling of 4-Arylthiocoumarins and Pyrones

被引：26
作者：
Zhang, Jin [1 ]
Zhuang, Yuyu [1 ]
Ma, Yangmin [1 ]
Yang, Xiufang [1 ]
Szostak, Michal [1 ,2 ]
机构：
[1] Shaanxi Univ Sci & Technol, Coll Chem & Chem Engn, Shaanxi Key Lab Chem Addit Ind, Xian 710021, Shaanxi, Peoples R China
[2] Rutgers State Univ, Dept Chem, 73 Warren St, Newark, NJ 07102 USA
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2019年 / 361卷 / 24期
关键词：
benzothiophenes; sulfur heterocycles; sulfur; cross-dehydrogenative coupling; C-H functionalization; SP(3) C-H; 3-DIMENSIONAL HETEROCYCLES; REGIOSELECTIVE SYNTHESIS; EFFICIENT SYNTHESIS; ACTIVATION; BOND; BENZOPYRANONES; ANNULATION; 2-PYRONES; ANALOGS;
D O I：
10.1002/adsc.201901058
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
Benzothiophenes represent a pivotal class of sulfur heterocycles and their synthesis has attracted significant attention to generate bioactive scaffolds. Herein, we report a convergent, atom- and step-economic method for the synthesis benzothiophenes by cross-dehydrogenative coupling (CDC) of 4-arylthiocoumarins in good to excellent yields. We further demonstrate cross-dehydrogenative coupling of 4-arylthio-2-pyrones to afford alternative substitution of benzothiophenes. The presence of a labile ester carbonyl moiety provides functional handle for further functionalization by coumarin deconstruction. Most crucially, the manuscript demonstrates that the use of readily accessible templated synthesis has a significant potential for the rapid assembly of sulfur heterocycles by dehydrogenative coupling mechanism.
引用
收藏
页码：5709 / 5714
页数：6
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