Photocatalytic decarboxylative alkylation of silyl enol ether and enamide with N-(acyloxy)phthalimide using ammonium iodide

Abstract

Enamides and silyl enol ethers were alkylated to deliver products of N-acyl imines and ketones in the presence of a catalytic amount of N-tetrabutylammonium iodide (TBAI) under irradiation with purple light-emitting diodes (427 nm) at room temperature. A broad scope of tertiary, secondary, and primary alkylation products was achieved with good yields and tolerance of a variety of functional groups. The reactions proceed through the photoactivation of a transiently assembled electron donor–acceptor complex formed between iodide and N-(acyloxy)phthalimide to generate alkyl radicals. The simplicity and low-cost nature of these methods without using metal catalysts demonstrate the practicality of the use of alkyl carboxylates as alkyl sources in organic synthesis.