4.7 Article

Halogen-Bonding-Promoted Photoinduced C-X Borylation of Aryl Halide Using Phenol Derivatives

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 88, Issue 9, Pages 6176-6181

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.3c00201

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This study investigates the photoinduced C-X borylation reaction of aryl halides via the formation of a halogen-bonding (XB) complex using 2-naphthol as an XB acceptor. The method is chemoselective and tolerant to a broad range of functional groups, providing a concise route to corresponding boronate esters. Mechanistic studies reveal that the formation of the XB complex between aryl halide and naphthol acts as an electron donor-acceptor complex, generating aryl radicals through photoinduced electron transfer.
This study investigates the photoinduced C-X borylation reaction of aryl halides by forming a halogen-bonding (XB) complex using 2-naphthol as an XB acceptor. The method is chemoselective and broadly functional group tolerant and provides concise access to corresponding boronate esters. Mechanistic studies reveal that forming the XB complex between aryl halide and naphthol acts as an electron donor-acceptor complex to furnish aryl radicals through photoinduced electron transfer.

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