Visible Light Induced Rhodium(I)‐Catalyzed C−H Borylation

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−RhI complex capable of both harvesting visible light and enabling the bond breaking/forming at room temperature. The chelating natur...

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Published inAngewandte Chemie International Edition Vol. 58; no. 43; pp. 15244 - 15248
Main Authors Thongpaen, Jompol, Manguin, Romane, Dorcet, Vincent, Vives, Thomas, Duhayon, Carine, Mauduit, Marc, Baslé, Olivier
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 21.10.2019
Wiley Subscription Services, Inc
Wiley-VCH Verlag
EditionInternational ed. in English
Subjects
boron
carbenes
Chelation
Chemical Sciences
Chemistry
Chemistry, Multidisciplinary
C−H activation
Diodes
Hydrogen bonds
Irradiation
Photocatalysis
photochemistry
Physical Sciences
Radiation
Rhodium
Science & Technology
ACTIVATION
EXCITED-STATE
HETEROCYCLIC CARBENE LIGANDS
ARYLATION
carbenes
SIGMA-BOND METATHESIS
FUNCTIONALIZATION
C-H activation
photochemistry
CATALYZED BORYLATION
MULTICOMPONENT SYNTHESIS
boron
METAL-COMPLEXES
TRANSFORMATIONS
rhodium
C−H activation
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Summary: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−RhI 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 RhI 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 RhIII‐hydride intermediate. Double agent: 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−RhI complex capable of both harvesting visible light and enabling the bond breaking/forming at room temperature. The bidentate structure of the NHC ligand was shown to be critical both for the stability and the reactivity of the RhI complex.
Bibliography:Medline
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201905924