Photocatalytic hydroalkylation of 3-methyleneisoindolin-1-ones with unactivated alkyl iodides

Abstract

We report herein a simple method for hydroalkylation of 3-methyleneisoindolin-1-ones with unactivated iodoalkanes using visible light photocatalysis and a halogen atom transfer (XAT) process. This operationally simple method exhibits broad substrate scope and allows late-stage modifications of iodoalkanes derived from either active pharmaceutical ingredients or natural products, producing a range of structurally diverse and valuable corresponding hydroalkylation products in decent yields. The generation of alkyl radicals and carbanion intermediates was directly proven in the catalytic cycle through radical trapping/radical clock and isotope labeling studies, respectively.