Anthranil: An Aminating Reagent Leading to Bifunctionality for Both C(sp3)−H and C(sp2)−H under Rhodium(III) Catalysis,Angewandte Chemie International Edition

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Anthranil: An Aminating Reagent Leading to Bifunctionality for Both C(sp3)−H and C(sp2)−H under Rhodium(III) Catalysis
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2016-04-28 , DOI: 10.1002/anie.201602224
Songjie Yu ₁ , Guodong Tang ₁ , Yingzi Li ₂ , Xukai Zhou ₁ , Yu Lan ₂ , Xingwei Li ₁

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Previous direct C−H nitrogenation suffered from simple amidation/amination with limited atom‐economy and is mostly limited to C(sp²)−H substrates. In this work, anthranil was designed as a novel bifunctional aminating reagent for both C(sp²)−H and C(sp³)−H bonds under rhodium(III) catalysis, thus affording a nucleophilic aniline tethered to an electrophilic carbonyl. A tridendate rhodium(III) complex has been isolated as the resting state of the catalyst, and DFT studies established the intermediacy of a nitrene species.

中文翻译：

蒽醌：在铑（III）催化下导致C（sp3-）-H和C（sp2-）-H都具有双功能的胺化试剂

以前的直接CH H氮化反应受简单的酰胺化/胺化作用和原子经济的限制，并且大多限于C（sp ²）-H底物。在这项工作中，将蒽醌设计为在铑（III）催化下同时用于C（sp ²）-H和C（sp ³）-H键的新型双功能胺化试剂，从而提供了拴接到亲电羰基的亲核苯胺。已经分离出三登酸盐铑（III）配合物作为催化剂的静止状态，DFT研究确定了亚硝基物质的中间体。

更新日期：2016-04-28

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