Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2013, Issue 29, Pages 6540-6544Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201300954
Keywords
Diazo compounds; Carbenoids; Wittig reactions; Hypervalent compounds; Iodonium ylides
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Funding
- Department of Chemistry, University of Waterloo
- Natural Sciences and Engineering Research Council of Canada (NSERC)
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A proof of concept study was undertaken to determine the suitability of monocarbonyl iodonium ylides (MCIYs) as metallocarbene precursors. Exposing Wittig reagents to iodosylbenzene results in a pseudo-Wittig reaction that generates MCIYs in situ. These ylides are intercepted by transition-metal catalysts to generate metallocarbenes, which then undergo either dimerization or cyclopropanation reactions with a variety of alkenes. Additionally, the reaction between diazoester-derived metallocarbenes and Wittig reagents afforded cross-coupling products, illustrating a new type of olefination reaction for phosphonium ylides.
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