Transition-metal-free homologative cross-coupling of aldehydes and ketones with geminal bis (boron) compounds

Stephens, Thomas and Pattison, Graham (2017) Transition-metal-free homologative cross-coupling of aldehydes and ketones with geminal bis (boron) compounds. Organic Letters, 19 (13). pp. 3498-3501. ISSN 1523-7060

Full content URL: https://doi.org/10.1021/acs.orglett.7b01474

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Transition-metal-free homologative cross-coupling of aldehydes and ketones with geminal bis (boron) compounds
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Abstract

We report a transition-metal-free coupling of aldehydes and ketones with geminal bis(boron) building blocks which provides the coupled, homologated carbonyl compound upon oxidation. This reaction not only extends an alkyl chain containing a carbonyl group, it also simultaneously introduces a new carbonyl substituent. We demonstrate that enantiopure aldehydes with an enolizable stereogenic center undergo this reaction with complete retention of stereochemistry.

Keywords:Boron, ketones, homologation
Subjects:F Physical Sciences > F100 Chemistry
Divisions:College of Science > School of Chemistry
ID Code:52244
Deposited On:31 Oct 2022 14:32

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