Relay cross metathesis reactions of vinylphosphonates

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Relay cross metathesis reactions of vinylphosphonates

Dimethyl (β-substituted) vinylphosphonates do not readily undergo cross metathesis reactions with Grubbs catalyst and terminal alkenes. However, the corresponding mono- or diallyl vinylphosphonate esters undergo facile cross metathesis reactions. The improved reactivity is attributed to a relay step in the cross metathesis reaction mechanism.

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Efficiency in olefin cross-metathesis reactions is affected upon reducing the steric bulk of N-heterocyclic carbene ligands of ruthenium-based catalysts. For the formation of disubstituted olefins containing one or more allylic substituents, the catalyst bearing N-tolyl groups is more efficient than the corresponding N-mesityl catalyst. In contrast, the formation of trisubstituted olefins is mo...

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Metathesis reactions in total synthesis.

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ژورنال

عنوان ژورنال: Beilstein Journal of Organic Chemistry

سال: 2014

ISSN: 1860-5397

DOI: 10.3762/bjoc.10.201