Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 145, Issue 11, Pages 6270-6279Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.2c12869
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An electrochemically driven nickel-catalyzed enantioselective reductive cross-coupling reaction was developed for the synthesis of enantioenriched beta-aryl homoallylic amines with excellent E-selectivity. This reaction proceeds under mild conditions without the use of heterogeneous metal reductants and sacrificial anodes, employing constant current electrolysis with triethylamine as a terminal reductant. The reaction demonstrates remarkable stereocontrol, broad substrate scope, and excellent functional group compatibility, making it suitable for the late-stage modification of bioactive molecules.
An electrochemically driven nickel-catalyzed enantioselective reductive cross-coupling of aryl aziridines with alkenyl bromides has been developed, affording enantioenriched beta-aryl homoallylic amines with excellent E-selectivity. This electroreductive strategy proceeds in the absence of heterogeneous metal reductants and sacrificial anodes by employing constant current electrolysis in an undivided cell with triethylamine as a terminal reductant. The reaction features mild conditions, remarkable stereocontrol, broad substrate scope, and excellent functional group compatibility, which was illustrated by the late-stage functionalization of bioactive molecules. Mechanistic studies indicate that this transformation conforms with a stereoconvergent mechanism in which the aziridine is activated through a nucleophilic halide ring-opening process.
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