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Synthesis of α,β-unsaturated aldehydes based on a one-pot phase-switch dehydrogenative cross-coupling of primary alcohols

Mura, Manuel G. and De Luca, Lidia Vera Giovanna and Taddei, Maurizio and Williams, Jonathan M.J. and Porcheddu, Andrea (2014) Synthesis of α,β-unsaturated aldehydes based on a one-pot phase-switch dehydrogenative cross-coupling of primary alcohols. Organic Letters, Vol. 16 (10), p. 2586-2589. ISSN 1523-7060. eISSN 1523-7052. Article.

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DOI: 10.1021/ol500916g

Abstract

An efficient one-pot ruthenium-catalyzed hydrogen-transfer strategy for a direct access to α,β-unsaturated aldehydes has been developed. The employment of enolates prepared in situ from alcohols avoided handling unstable aldehydes and provided a very appealing route to different cinnamaldehydes substituted in position 2. A silica-grafted amine was used as phase-switch tag leading to a selective one-pot process in favor of cross-dehydrogenative coupling products.

Item Type:Article
ID Code:9890
Status:Published
Refereed:Yes
Uncontrolled Keywords:α,β-unsaturated aldehydes, one-pot ruthenium-catalyzed hydrogen-transfer strategy, primary alcohols
Subjects:Area 03 - Scienze chimiche > CHIM/06 Chimica organica
Divisions:001 Università di Sassari > 01-a Nuovi Dipartimenti dal 2012 > Chimica e Farmacia
Publisher:American Chemical Society
ISSN:1523-7060
eISSN:1523-7052
Deposited On:19 Jun 2014 12:50

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