Amine Carboxyborane: A Versatile Ligated Boryl Radical Precursor

21 August 2024, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Amine carboxyborane has been demonstrated as a novel precursor for amine-ligated boryl radicals. The anion of amine carboxyborane was effectively oxidized using a 5CzBN photocatalyst under blue LED light, with subsequent decarboxylation facilitating the generation of ligated boryl radicals. This process enabled an efficient halogen atom transfer (XAT) with alkyl bromides, resulting in Giese addition products with various electron-deficient double bonds. Moreover, direct addition of several boryl radicals was also possible using ligated carboxyboranes.

Keywords

amine carboxyborane
amine-ligated boryl radical
halogen atom transfer
Giese reaction

Supplementary materials

Title
Description
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Title
Amine Carboxyboane
Description
Amine carboxyborane was demonstrated as a versatile precursor for the generation of amine-ligated boryl radical. Its anion has low oxidation potential and was employed in reductive quenching photocatalysis. Geise reaction of alkyl and boryl radical was enabled using various amine carboxyborane and CV measurement and DFT calculation support the proposed mechanism.
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