期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 54, 期 22, 页码 6604-6607出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201501287
关键词
C(sp(3))P bonds; copper catalysis; oxidative coupling; radical; radical cross-coupling; -ketophosphonates
资金
- 973 Program [2012CB725302, 2011CB808600]
- National Natural Science Foundation of China [21390400, 21272180, 21302148]
- Research Fund for the Doctoral Program of Higher Education of China [20120141130002]
- Program for Changjiang Scholars and Innovative Research Team in University [IRT1030]
- Ministry of Science and Technology of China [2012YQ120060]
- Program of Introducing Talents of Discipline to Universities of China (111 Program)
The selective radical/radical cross-coupling of two different organic radicals is a great challenge due to the inherent activity of radicals. In this paper, a copper-catalyzed radical/radical Csp3H/PH cross-coupling has been developed. It provides a radical/radical cross-coupling in a selective manner. This work offers a simple way toward -ketophosphonates by oxidative coupling of aryl ketone o-acetyloximes with phosphine oxides using CuCl as catalyst and PCy3 as ligand in dioxane under N-2 atmosphere at 130 degrees C for 5h, and yields ranging from 47% to 86%. The preliminary mechanistic studies by electron paramagnetic resonance (EPR) showed that, 1)the reduction of ketone o-acetyloximes generates iminium radicals, which could isomerize to -sp(3)-carbon radical species; 2)phosphorus radicals were generated from the oxidation of phosphine oxides. Various aryl ketone o-acetyloximes and phosphine oxides were suitable for this transformation.
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