Rhoda-Electrocatalyzed C-H Methylation and Paired Electrocatalyzed C-H Ethylation and Propylation

Chemistry. 2022 Jan 3;28(1):e202103837. doi: 10.1002/chem.202103837. Epub 2021 Nov 10.

Abstract

The use of electricity over traditional stoichiometric oxidants is a promising strategy for sustainable molecular assembly. Herein, we describe the rhoda-electrocatalyzed C-H activation/alkylation of several N-heteroarenes. This catalytic approach has been successfully applied to several arenes, including biologically relevant purines, diazepam, and amino acids. The versatile C-H alkylation featured water as a co-solvent and user-friendly trifluoroborates as alkylating agents. Finally, the rhoda-electrocatalysis with unsaturated organotrifluoroborates proceeded by paired electrolysis.

Keywords: C−H activation; electrochemistry; methylation; paired electrolysis; rhodium.

MeSH terms

  • Alkylation
  • Catalysis
  • Methylation*