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用于吡咯和内酯合成的双叉状铑电催化C-H活化反应

Bifurcated Rhodaelectro-catalyzed C-H Activation for the Synthesis of Pyrroles and Lactones.

作者信息

Homölle Simon L, Stangier Maximilian, Reyes Efraim, Ackermann Lutz

机构信息

Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstraße 2, 37077 Göttingen, Germany.

University of the Basque Country (UPV/EHU), Barrio Sarriena s/n, 48940 Leioa, Bizkaia, Spain.

出版信息

Precis Chem. 2023 Jul 20;1(6):382-387. doi: 10.1021/prechem.3c00061. eCollection 2023 Aug 28.

Abstract

While electrocatalyzed alkyne annulations of arenes represent a powerful strategy for the assembly of heteroaromatic motives, electrochemical C(sp)-H activations of alkenes remain scarce. Herein, a strategy for the rhodaelectro-catalyzed functionalization of enamides is presented for the efficient construction of pyrroles using electricity as a sustainable oxidant. Moreover, the tuning of the solvent system allowed a fascinating switch in chemoselectivity, which is not possible with traditionally used chemical oxidants, giving rise to lactone architectures. The rhoda-electrocatalysis features a broad scope as well as high regio- and chemoselectivities.

摘要

虽然芳烃的电催化炔烃环化反应是构建杂芳环结构的有力策略,但烯烃的电化学C(sp)-H活化反应仍然很少见。本文提出了一种铑电催化烯酰胺官能化的策略,以电作为可持续氧化剂高效构建吡咯。此外,溶剂体系的调节实现了化学选择性的迷人转变,这是传统化学氧化剂无法实现的,从而产生了内酯结构。铑电催化具有广泛的底物范围以及高区域选择性和化学选择性。

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