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DOI: 10.1055/s-0030-1260065
Olefination Reactions Using Tetraarylphosphonium (TAP)-Supported Phosphorus Ylides
Publication History
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
- Supporting Information for this article is available online:
- Supporting Information
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References
Although the crude NMR spectra showed >90% product purity, flash chromatography was performed to remove diethyl fumarate and maleate formed from ethyl diazoacetate.
15When 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.