Issue 15, 2021

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.

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

Supplementary files

Article information

Article type
Research Article
Submitted
26 Apr 2021
Accepted
27 May 2021
First published
02 Jun 2021

Org. Chem. Front., 2021,8, 4166-4170

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

C. Liu, N. Shen and R. Shang, Org. Chem. Front., 2021, 8, 4166 DOI: 10.1039/D1QO00648G

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