C-Alkylation of N-alkylamides with styrenes in air and scale-up using a microwave flow reactor

Org Biomol Chem. 2018 Nov 7;16(41):7568-7573. doi: 10.1039/c8ob02282h. Epub 2018 Oct 9.

Abstract

C-Alkylation of N-alkylamides with styrenes is reported, proceeding in ambient air/moisture to give arylbutanamides and pharmaceutically-relevant scaffolds in excellent mass balance. Various amide and styrene derivatives were tolerated, rapidly affording molecular complexity in a single step; thus highlighting the future utility of this transformation in the synthetic chemistry toolbox. Reaction scalability (up to 65 g h-1 product) was demonstrated using a Microwave Flow reactor, as the first example of a C-alkylation reaction using styrenes in continuous flow.

Publication types

  • Research Support, Non-U.S. Gov't