Nickel-Catalyzed Electroreductive Heck Reaction: A Divergent Synthesis of C7- or C2-Arylindolines
Yongjie Yang1, Balati Hasimujiang1, Zaimu Cao1
1Guangzhou Municipal and Guangdong Provincial Key Laboratory of Molecular Target & Clinical Pharmacology and the State Key Laboratory of Respiratory Disease, School of Pharmaceutical Sciences, Guangzhou Medical University, Guangzhou 511436, People's Republic of China.
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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