Decarboxylative Acetoxylation of Aliphatic Carboxylic Acids

Organic molecules bearing acetoxy moieties are important functionalities in natural products, drugs, and agricultural chemicals. Synthesis of such molecules via transition metal-catalyzed C–O bond formation can be achieved in the presence of a carefully chosen directing group to alleviate the challe...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2019-10, Vol.84 (19), p.12553-12561
Main Authors: Senaweera, Sameera, Cartwright, Kaitie C, Tunge, Jon A
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Organic molecules bearing acetoxy moieties are important functionalities in natural products, drugs, and agricultural chemicals. Synthesis of such molecules via transition metal-catalyzed C–O bond formation can be achieved in the presence of a carefully chosen directing group to alleviate the challenges associated with regioselectivity. An alternative approach is to use ubiquitous carboxylic acids as starting materials and perform a decarboxylative coupling. Herein, we report conditions for a photocatalytic decarboxylative C–O bond formation reaction that provides rapid and facile access to the corresponding acetoxylated products. Mechanistic investigations suggest that the reaction operates via oxidation of the carboxylate followed by rapid decarboxylation and oxidation by Cu­(OAc)2.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b02092