Access to aliphatic ester derivatives via visible-light-induced radical alkoxycarbonylation of unactivated alkenes

Abstract

This study presents a robust novel strategy for the alkoxycarbonyl difunctionalization of unactivated alkenes. Using the alkoxycarbonyl radical donors we previously designed and synthesized, photoinduced efficient generation of alkoxycarbonyl radicals with varying carbon chain lengths enables addition to unactivated alkenes, which triggers intramolecular distal functional group migration, successfully affording aliphatic carboxylate derivatives. This protocol features a broad substrate scope and mild reaction conditions, and its potential synthetic utility was further evidenced by compatibility tests with natural product-derived molecules, scale-up reactions, and subsequent derivatizations.