Photocatalytic decarboxylative alkylation of silyl enol ether and enamide with N-(acyloxy)phthalimide using ammonium iodide. Issue 15 (10th June 2021)

• Record Type: Journal Article
• Authors: Liu, Can; Shen, Ni; Shang, Rui
• Is Part Of: Organic chemistry frontiers. Volume 8:Issue 15(2021)
• Page Start: 4166
• Page End: 4170
• Publication Date: 2021-06-10
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d1qo00648g
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : Under visible light, a catalytic amount of ammonium iodide promotes the decarboxylative alkylation of silyl enol ether and enamide with aliphatic N -(acyloxy)phthalimide through the photoactivation of a transiently assembled chromophore. 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.