Visible-Light-Induced External Oxidant-Free Oxidative Phosphonylation of C(sp2)–H Bonds

Considering the synthetic value of phosphonates, developing powerful catalytic methods for the phosphonylation of C­(sp2)–H bonds is important. Herein, we achieve a visible-light-induced external oxidant-free oxidative phosphonylation of C­(sp2)–H bonds via the combination of photocatalysis and prot...

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Veröffentlicht in:ACS catalysis 2017-11, Vol.7 (11), p.7412-7416
Hauptverfasser: Niu, Linbin, Liu, Jiamei, Yi, Hong, Wang, Shengchun, Liang, Xing-An, Singh, Atul K, Chiang, Chien-Wei, Lei, Aiwen
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container_end_page 7416
container_issue 11
container_start_page 7412
container_title ACS catalysis
container_volume 7
creator Niu, Linbin
Liu, Jiamei
Yi, Hong
Wang, Shengchun
Liang, Xing-An
Singh, Atul K
Chiang, Chien-Wei
Lei, Aiwen
description Considering the synthetic value of phosphonates, developing powerful catalytic methods for the phosphonylation of C­(sp2)–H bonds is important. Herein, we achieve a visible-light-induced external oxidant-free oxidative phosphonylation of C­(sp2)–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(sp2)–H bonds, especially for those that are sensitive to oxidative conditions.
doi_str_mv 10.1021/acscatal.7b02418
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title Visible-Light-Induced External Oxidant-Free Oxidative Phosphonylation of C(sp2)–H Bonds
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