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Synthesis 2011(14): 2275-2280  
DOI: 10.1055/s-0030-1260065
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Olefination Reactions Using Tetraarylphosphonium (TAP)-Supported Phosphorus Ylides

Hélène Lebel*, Michaël Davi, Marie-Noelle Roy, Walid Zeghida, André B. Charette*
Department of Chemistry and Centre in Green Chemistry and Catalysis (CGCC), Université de Montréal, Pavillon Roger Gaudry, 2900 Boul. Édouard-Montpetit, Montréal, QC, H3T 1J4, Canada, Fax: +1(514)3437586; helene.lebel@umontreal.ca
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Publication History

Received 11 March 2011
Publication Date:
10 June 2011 (online)

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Abstract

Tetraarylphosphonium (TAP)-supported phosphorus ylides were prepared and used in copper-catalyzed olefination reactions with diazo compounds to produce conjugated esters, amides, and phosphonates. The TAP-phosphine oxide can easily be separated from the alkene product, recycled, and reused.

Key words

alkenes - diazo compounds - green chemistry - Wittig reaction - ylides

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9

Although the crude NMR spectra showed >90% product purity, flash chromatography was performed to remove diethyl fumarate and maleate formed from ethyl diazoacetate.

15

When unreacted aldehyde was present, the filtrate was stirred with aq 10% NaHSO3 (3 mL) at r.t. for 1 h. The two layers were separated and the organic layer was washed with H2O (3 mL), dried (MgSO4), and concentrated under reduced pressure to afford a pure mixture of E- and Z-olefin isomers.