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

Xiaowei Zhang; Sheng Wang; Chanjuan Xi

doi:10.1021/acs.joc.9b01587

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

J Org Chem. 2019 Aug 2;84(15):9744-9749. doi: 10.1021/acs.joc.9b01587. Epub 2019 Jul 23.

Authors

Xiaowei Zhang¹, Sheng Wang¹, Chanjuan Xi^{1

2}

Affiliations

¹ MOE Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology, Department of Chemistry , Tsinghua University , Beijing 100084 , China.
² State Key Laboratory of Elemento-Organic Chemistry , Nankai University , Tianjin 300071 , China.

PMID: 31290305
DOI: 10.1021/acs.joc.9b01587

Abstract

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(sp³)-H bonds. A variety of 2-arylpropionitrile was obtained in good yields. The reaction could also be applied at the gram scale.