4.7 Article

alpha-Methylation of 2-Arylacetonitrile by a Trimethylamine-Borane/CO2 System

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 15, Pages 9744-9749

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b01587

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Funding

  1. National Natural Science Foundation of China [91645120, 21871163]

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A highly selective monomethylation of 2-arylacetonitrile using CO2 is described. The utilization of trimethylamine-borane facilitates the six-electron reduction of CO2. This reaction is the first selective six-electron reductive functionalization of CO2 faciliated by C(sp(3))-H bonds. A variety of 2-arylpropionitrile was obtained in good yields. The reaction could also be applied at the gram scale.

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