Photoinduced Decarboxylative Amino-Fluoroalkylation of Maleic Anhydride

Chemistry. 2020 Jan 7;26(2):419-422. doi: 10.1002/chem.201904751. Epub 2019 Dec 5.

Abstract

A photoinduced decarboxylative three-component coupling reaction involving amine, maleic anhydride, and fluorinated alkyl iodides has been developed, leading to synthetically valuable fluoroalkyl-containing acrylamides with a high E selectivity. A broad array of substrates including monoprotected amino acid are capable coupling partners. Preliminary mechanistic studies suggest a stepwise process. This reaction represents the first example of photoinduced decarboxylative difunctionalization of maleic anhydride.

Keywords: E selectivity; decarboxylative; fluoroalkyl-containing acrylamides; photoinduced; three-component reactions.