Palladium-catalyzed dearomative Heck/[4 + 3] decarboxylative cyclization of indoles with α-oxocarboxylic acids via C−H activation

IF 4.6 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2024-12-19 DOI:10.1039/d4qo02024c

Liwei Zhou, Pengyang Jing, Wenbo Deng, Shuyi Guo, Yun Liang, Yuan Yang

引用次数: 0

Abstract

Herein, we report a novel palladium-catalyzed dearomative Heck/[4 + 3] decarboxylative cyclization of C2-tethered indoles with α-oxocarboxylic acids via C−H activation. In this reaction, dearomatization of C2-tethered indoles occurs via a Heck reaction pathway, leading to the formation of the alkyl-Pd(II) species. Subsequently, this species undergoes C−H activation, rather than the typical nucleophilic trapping or β−H elimination, to generate C,C-palladacycles, which are then captured by α-oxocarboxylic acids to afford hexacyclic and octocyclic fused indolines containing a seven-membered ring.

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来源期刊

Organic Chemistry Frontiers CHEMISTRY, ORGANIC-

CiteScore

7.90

自引率

11.10%

发文量

686

审稿时长

1 months

期刊介绍： Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.