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Transition Metal Free sp³-sp³ carbon-carbon coupling between Benzylboronic Esters and Alkyl Bromides.

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.

SUBMITTER: Russell RW

PROVIDER: S-EPMC8966628 | biostudies-literature | 2021 May

REPOSITORIES: biostudies-literature

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Transition Metal Free sp3-sp3 carbon-carbon coupling between Benzylboronic Esters and Alkyl Bromides.

Russell Richard W RW Barker Timothy J TJ

European journal of organic chemistry 20210423 19

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. Mec ...[more]

PMID: 35370453

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