Issue 7, 2023

Metal -free PhI(OAc)2-oxidized decarboxylation of propiolic acids towards synthesis of α-acetoxy ketones and insights into general decarboxylation with DFT calculations

Abstract

A metal-free oxidative decarboxylation reaction of propiolic acids mediated by hypervalent iodine(III) reagents is described. This decarboxylative C–O bond-forming reaction used a combination of (diacetoxyiodo)benzene and aromatic, heteroaromatic or aliphatic propiolic acids to give the corresponding α-acetoxy ketones. Preliminary mechanistic studies based on both DFT calculations and high-resolution mass spectroscopy (HRMS) suggested that the reaction proceeded through decarboxylation to form a propargyl iodide intermediate. This reaction provides an attractive alternative to existing methods for the exclusive synthesis of α-acyloxy ketones.

Graphical abstract: Metal -free PhI(OAc)2-oxidized decarboxylation of propiolic acids towards synthesis of α-acetoxy ketones and insights into general decarboxylation with DFT calculations

Supplementary files

Article information

Article type
Paper
Submitted
19 Dec 2022
Accepted
30 Dec 2022
First published
03 Jan 2023

Org. Biomol. Chem., 2023,21, 1457-1462

Metal -free PhI(OAc)2-oxidized decarboxylation of propiolic acids towards synthesis of α-acetoxy ketones and insights into general decarboxylation with DFT calculations

T. Gao, Y. Yang, L. Hu, D. Luo, X. Zhang and Y. Xiong, Org. Biomol. Chem., 2023, 21, 1457 DOI: 10.1039/D2OB02281H

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