Organic Chemistry

Halogen-bonding-promoted Photo-induced C–X Borylation of Aryl Halide using Phenol Derivatives

Authors

Abstract

This study investigates the photo-induced C–X borylation reaction of aryl halides by forming a halogen-bonding complex. The method employs 2-naphthol as a halogen-bonding acceptor and proceeds under mild conditions without a photoredox catalyst under 420 nm blue light irradiation. The method is highly chemoselective, broadly functional group tolerant, and provides concise access to corresponding boronate esters. Mechanistic studies reveal that forming the halogen-bonding complex between aryl halide and naphthol acts as an electron donor-acceptor complex to furnish aryl radicals through photo-induced electron transfer.

Version notes

manuscript and SI were revised

Content

Thumbnail image of 20221130.pdf

Supplementary material

Thumbnail image of 20221130.pdf
ESI_Halogen-bonding-promoted Photo-induced C–X Borylation of Aryl Halide using Phenol Derivatives
UV/Vis spectra, results of full detailed optimization study experiments, and characterization of all compounds synthesized.
Thumbnail image of SI_NMR.pdf
ESI_Halogen-bonding-promoted Photo-induced C–X Borylation of Aryl Halide using Phenol Derivatives_2
1H, 13C{1H} and 19F NMR spectra of all compounds.