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Transition Metal‐Free sp 3 −sp 3 Carbon‐Carbon Coupling between Benzylboronic Esters and Alkyl Bromides
Author(s) -
Russell Richard W.,
Barker Timothy J.
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100361
Subject(s) - chemistry , alkyl , chemoselectivity , nucleophile , halide , electrophile , transition metal , beta hydride elimination , medicinal chemistry , bromide , coupling reaction , organic chemistry , catalysis
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 for the reaction with the alkyl bromide in substrates with a second electrophile present. Both secondary and tertiary benzylboronic esters were effective nucleophiles in the reaction with primary alkyl halides. Mechanistic observations are consistent with a radical mechanism.