Computational Study on Catalyst-free BCl-promoted Chloroboration of Carbonyl Compounds

Overview

Journal RSC Adv

Publisher Royal Society of Chemistry

Date 2025 Jan 29

PMID 39877698

Authors

Abera Tadie Derese

Mengistu Gemech Menkir

Mihret Kendie Wolie

Desalegn Addis Yemam

Affiliations

Soon will be listed here.

Abstract

DFT calculations were performed to investigate the possible reaction mechanisms underlying catalyst-free chloroboration reactions of carbonyl compounds with BCl. The interaction between BCl and the C[double bond, length as m-dash]O moiety of carbonyl compounds is a two-step reaction. In the first step, B of BCl forms a bond with the O of the C[double bond, length as m-dash]O moiety, followed by the 1,3-Cl migration process from BCl to the C of the carbonyl group. To indicate the versatility of our synthetic methodology, a catalyst-free chloroboration of a variety of aldehydes and ketones with a broad range of electron-donating and electron-withdrawing groups with BCl was checked. According to DFT results, BCl-induced chloroboration of aldehydes and ketones progressed under a kinetically favorable condition with <20 kcal mol of activation free energy.

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