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铜催化的通过直接氧化活化芳基 C(sp)-N 键的脱氢 C(sp)-N 键形成反应:苯并咪唑并[1,2-a]吲哚的合成。

Copper-Catalyzed Dehydrogenative C(sp)-N Bond Formation via Direct Oxidative Activation of an Anilidic N-H Bond: Synthesis of Benzoimidazo[1,2-a]indoles.

机构信息

Department of Chemistry, Capital Normal University , Beijing, 100048, P. R. China.

Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University , Beijing 100084, P. R. China.

出版信息

J Org Chem. 2017 Oct 6;82(19):10158-10166. doi: 10.1021/acs.joc.7b01617. Epub 2017 Sep 13.

Abstract

A dehydrogenative C(sp)-N bond-forming strategy via copper-catalyzed intramolecular C-H/N-H coupling has been developed, which systematically unraveled the feasibility and practicality for benzoimdazo[1,2-a]indole formations through oxidative anilidic N-H activation. The merit of this strategy is illustrated by the broad tolerance of functionalities, as well as the utilization of extremely cheap copper catalysis to realize potentially useful indole-fused tetracycles in a step- and atom-economical manner.

摘要

一种通过铜催化的分子内 C-H/N-H 偶联实现的脱氢 C(sp)-N 键形成策略已经被开发出来,该策略通过氧化苯胺 N-H 活化系统地揭示了苯并咪唑并[1,2-a]吲哚形成的可行性和实用性。该策略的优点在于其官能团的广泛耐受性,以及利用极其廉价的铜催化以一步原子经济性的方式实现潜在有用的吲哚稠合四环化合物。

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