Nickel-Catalyzed Electroreductive Heck Reaction: A Divergent Synthesis of C7- or C2-Arylindolines

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-04-09 DOI:10.1021/acs.orglett.5c0049510.1021/acs.orglett.5c00495

Yongjie Yang, Balati Hasimujiang, Zaimu Cao, Qingbin Yuan, Xinwei Hu* and Zhixiong Ruan*,

引用次数: 0

Abstract

Herein, we present a novel electrochemically driven nickel-catalyzed Heck reaction of readily available N-arylacrylindoles for the construction of both 7-arylindolines and 2-arylindolines. The reaction proceeds in an undivided electrochemical cell and employs a sacrificial zinc anode as the reductant. This catalytic protocol features a consecutive electroreductive process under exceedingly mild reaction conditions, with moderate yields. Detailed mechanistic studies indicate that the reaction involves a domino sequence of intramolecular electroreductive Heck arylation and selective C–C or C–O bond cleavage, which could be accomplished by aryl migration or carbethoxy removal.

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.