Cp*CoIII Catalyzed syn-Selective C-H Hydroarylation of Alkynes Using Benzamides: An Approach Toward Highly Conjugated Organic Frameworks

Cp*CoIII Catalyzed syn-Selective C-H Hydroarylation of Alkynes Using Benzamides: An Approach Toward Highly Conjugated Organic Frameworks
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DOI:
10.1021/acs.joc.6b02516
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发表时间:
2017-01-06
影响因子:
3.6
通讯作者:
Maji, Modhu Sudan
Maji, Modhu Sudan
中科院分区:
化学2区
文献类型:
--
作者:
Bera, Sourav Sekhar;Debbarma, Suvankar;Maji, Modhu Sudan

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在 N-叔丁基酰胺的指导下,通过成本有效的 Cow 催化实现内部炔烃的加氢芳基化,以原子和步骤经济的方式选择性地获得单或二氢芳基化酰胺产物。几个重要的官能团在反应条件下都可以耐受,并且顺式加氢芳基化产物被完全分离。值得注意的是,4 重 C-H 加氢芳基化一步提供了高度共轭的有机框架。进行了广泛的氘标记实验的动力学研究以支持所提出的机制。
Hydroarylation of internal alkynes by costeffective Cow-catalysis, directed by N-tert-butyl amides, is achieved to avail mono- or dihydroarylated amide products selectively in an atom and step economic way. Several important functional groups were tolerated under the reaction conditions, and syn-hydroarylation products were exclusively isolated. Notably, a 4-fold C-H hydroarylation provided a highly conjugated organic framework in one step. Kinetic study with extensive deuterium labeling experiments were performed to support the proposed mechanism.