Issue 34, 2020

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


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.

Graphical abstract: Deoxygenative α-alkylation and α-arylation of 1,2-dicarbonyls

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Article information

Article type
Edge Article
03 Jun 2020
30 Jun 2020
First published
01 Jul 2020
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2020,11, 9101-9108

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

S. Jin, H. T. Dang, G. C. Haug, V. D. Nguyen, H. D. Arman and O. V. Larionov, Chem. Sci., 2020, 11, 9101 DOI: 10.1039/D0SC03118F

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