Ethylene-Promoted versus Ethylene-Free Enyne Metathesis

The role of ethylene in promoting metathesis of acetylenic enynes is probed within the context of ring-closing enyne metathesis, using first- and second-generation Grubbs catalysts. Under inert atmosphere, rapid catalyst deactivation is observed by calibrated GC–FID analysis for substrates with mini...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2011-10, Vol.133 (40), p.15918-15921
Main Authors: Grotevendt, Anne G. D, Lummiss, Justin A. M, Mastronardi, Melanie L, Fogg, Deryn E
Format: Article
Language:English
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Summary:The role of ethylene in promoting metathesis of acetylenic enynes is probed within the context of ring-closing enyne metathesis, using first- and second-generation Grubbs catalysts. Under inert atmosphere, rapid catalyst deactivation is observed by calibrated GC–FID analysis for substrates with minimal propargylic bulk. MALDI-TOF mass spectra reveal a Ru(enyne)2 derivative that exhibits very low reactivity toward both enyne and ethylene. Under ethylene, formation of this species is suppressed. Enynes with bulky propargylic groups are not susceptible to this catalyst deactivation pathway, even under N2 atmosphere.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja207388v