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Deoxygenative α-alkylation and α-arylation of 1,2-dicarbonyls.

ABSTRACT: Construction of C-C bonds at the α-carbon is a challenging but synthetically indispensable approach to α-branched carbonyl motifs that are widely represented among drugs, natural products, and synthetic intermediates. Here, we describe a simple approach to generation of boron enolates in the absence of strong bases that allows for introduction of both α-alkyl and α-aryl groups in a reaction of readily accessible 1,2-dicarbonyls and organoboranes. Obviation of unselective, strongly basic and nucleophilic reagents permits carrying out the reaction in the presence of electrophiles that intercept the intermediate boron enolates, resulting in two new α-C-C bonds in a tricomponent process.

SUBMITTER: Jin S

PROVIDER: S-EPMC8161533 | biostudies-literature | 2020 Jul

REPOSITORIES: biostudies-literature

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Deoxygenative α-alkylation and α-arylation of 1,2-dicarbonyls.

Jin Shengfei S Dang Hang T HT Haug Graham C GC Nguyen Viet D VD Arman Hadi D HD Larionov Oleg V OV

Chemical science 20200701 34

Construction of C-C bonds at the α-carbon is a challenging but synthetically indispensable approach to α-branched carbonyl motifs that are widely represented among drugs, natural products, and synthetic intermediates. Here, we describe a simple approach to generation of boron enolates in the absence of strong bases that allows for introduction of both α-alkyl and α-aryl groups in a reaction of readily accessible 1,2-dicarbonyls and organoboranes. Obviation of unselective, strongly basic and nucl ...[more]

PMID: 34094191

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