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Transition Metal Free sp3-sp3 carbon-carbon coupling between Benzylboronic Esters and Alkyl Bromides
Richard W Russell1, Timothy J Barker1
1Department of Chemistry and Biochemistry, College of Charleston, Charleston, SC 29424.
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.
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