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Transition-Metal-Free Oxidative Decarboxylative Cross Coupling of α,β-Unsaturated Carboxylic Acids with Cyclic Ethers under Air Conditions: Mild Synthesis of α-Oxyalkyl Ketones.

Authors :
Peng-Yi Ji
Yu-Feng Liu
Jing-Wen Xu
Wei-Ping Luo
Qiang Liu
Can-Cheng Guo
Source :
Journal of Organic Chemistry. 3/17/2017, Vol. 82 Issue 6, p2965-2971. 7p.
Publication Year :
2017

Abstract

A novel K2S2O8-promoted decarboxylative cross coupling of α,β-unsaturated carboxylic acids with cyclic ethers was developed under aerobic conditions. The present protocol, which includes C-C and CO bond formation in one step through addition, oxidation, and decarboxylation processes, leads to the desired ketone products in moderate to excellent yields. In addition, mechanism studies showed that the transformation process undergoes a radical pathway via a direct activation of the α-sp³ C-H bond of oxygen of the cyclic ether. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
00223263
Volume :
82
Issue :
6
Database :
Academic Search Index
Journal :
Journal of Organic Chemistry
Publication Type :
Academic Journal
Accession number :
122575558
Full Text :
https://doi.org/10.1021/acs.joc.6b02993