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Visible Light Induced Rhodium(I)‐Catalyzed C−H Borylation
Author(s) -
Thongpaen Jompol,
Manguin Romane,
Dorcet Vincent,
Vives Thomas,
Duhayon Carine,
Mauduit Marc,
Baslé Olivier
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201905924
Subject(s) - borylation , rhodium , photocatalysis , chemistry , catalysis , visible spectrum , photochemistry , regioselectivity , hydride , ligand (biochemistry) , chelation , iridium , medicinal chemistry , polymer chemistry , organic chemistry , materials science , metal , biochemistry , alkyl , receptor , optoelectronics , aryl
Abstract An efficient visible light induced rhodium(I)‐catalyzed regioselective borylation of aromatic C−H bonds is reported. The photocatalytic system is based on a single NHC−Rh I complex capable of both harvesting visible light and enabling the bond breaking/forming at room temperature. The chelating nature of the NHC‐carboxylate ligand was critical to ensure the stability of the Rh I complex and to provide excellent photocatalytic activities. Experimental mechanistic studies evidenced a photooxidative ortho C−H bond addition upon irradiation with blue LEDs, leading to a cyclometalated Rh III ‐hydride intermediate.