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Issue 24, 2018
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Direct conjugate additions using aryl and alkyl organic halides in air and water

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Abstract

The direct aryl-conjugate addition to electron-deficient alkenes without prior stoichiometric formation of organometallic reagents in water catalyzed by copper represents an important but unresolved challenge. Herein, we describe a simple and convenient one-pot protocol for this type of conjugate addition. Compared with traditional methods that feature pre-formed stoichiometric organometallic reagents and strict anhydrous conditions, this transformation is actually performed in water and successfully applied to α,β-unsaturated esters, acrylonitriles and α,β-unsaturated phosphonates via direct arylation. Furthermore, this process is scalable and accommodates both aryl and alkyl halides. Importantly, the same reaction carried out in an organic solvent proceeded sluggishly to provide much inferior yields.

Graphical abstract: Direct conjugate additions using aryl and alkyl organic halides in air and water

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Supplementary files

Article information


Submitted
22 Oct 2018
Accepted
14 Nov 2018
First published
22 Nov 2018

Org. Chem. Front., 2018,5, 3579-3584
Article type
Research Article

Direct conjugate additions using aryl and alkyl organic halides in air and water

F. Zhou, X. Hu, W. Zhang and C. Li, Org. Chem. Front., 2018, 5, 3579 DOI: 10.1039/C8QO01141A

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