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

06 January 2022, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

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.

Keywords

C–X borylation
halogen bonding complex
aryl halides
photo reaction

Supplementary materials

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