Journal
ACS CATALYSIS
Volume 7, Issue 11, Pages 7412-7416Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.7b02418
Keywords
Photocatalysis; External oxidant-free; Proton-reduction catalysis; Phosphonylation; C(sp(2))-H bonds; Radical cation
Categories
Funding
- 973 Program [2011CB808600, 2012CB725302, 2013CB834804]
- National Natural Science Foundation of China [21390400, 21272180, 21302148, 2109343, 21402217]
- Research Fund for the Doctoral Program of Higher Education of China [20120141130002]
- Ministry of Science and Technology of China [2012YQ120060]
- Program for Changjiang Scholars and Innovative Research Team in University [IRT1030]
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Considering the synthetic value of phosphonates, developing powerful catalytic methods for the phosphonylation of C(sp(2))-H bonds is important. Herein, we achieve a visible-light-induced external oxidant-free oxidative phosphonylation of C(sp(2))-H bonds via the combination of photocatalysis and proton-reduction catalysis. Mechanistic studies indicate that the visible-light-induced electron-rich arene radical cation is the key reactive intermediate. The synthetic application of this approach is demonstrated in the late-stage functionalization of pharmaceutical molecules. This study may have significant implications for the functionalization of C(sp(2))-H bonds, especially for those that are sensitive to oxidative conditions.
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