Photoinduced Cerium-Mediated Decarboxylative Alkylation Cascade Cyclization of N-arylacrylamides and N-acryl-2-aryl benzimidazoles.

Abstract

A mild and versatile cerium-mediated decarboxylative strategy for sequential alkylation/cyclization was developed for the synthesis of quaternary oxindoles and benzimidazo[2,1-a]isoquinolin-6(5H)-ones via photoinduced-LMCT. This operationally simple procedure relies on inexpensive and feedstock carboxylic acids as alkyl radical surrogates and aerial molecular oxygen as the terminal oxidant. This mild and atom economical protocol showed viability with a wide range of alkyl carboxylic acids (1° to 3° acids) as coupling partners and also allows the late-stage modification of pharmaceutically-important acids. Mechanistic studies revealed the reaction to follow radical pathway, while the decarboxylative event was studied by in situ FTIR.