Work

Transition Metal‐Free sp3−sp3 Carbon‐Carbon Coupling between Benzylboronic Esters and Alkyl Bromides

Year: 2021

Type: article

Abstract: A transition metal free coupling reaction of benzylboronic esters and alkyl halides has been developed. Both alkyl bromides and alkyl iodides were found to be competent substrates with the nucleophilic boronate intermediate generated from the combination of benzylboronic ester and an alkyllithium. Good chemoselectivity was observed in substrates with a second electrophile. Both secondary and tertiary benzylboronic esters were effective nucleophiles in the reaction with primary alkyl halides. Mechanistic observations are consistent with a radical mechanism.

Source: European Journal of Organic Chemistry

DOI: 10.1002/ejoc.202100361

Authors: Richard W. Russell, Timothy J. Barker

Institution: College of Charleston

Language: English

Topic: Catalytic Cross-Coupling Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green