Merging Grubbs second-generation catalyst with photocatalysis enables <i>Z</i>-selective metathesis of olefins: scope, limitations, and mechanism - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Chemical Science Année : 2022

Merging Grubbs second-generation catalyst with photocatalysis enables Z-selective metathesis of olefins: scope, limitations, and mechanism

Résumé

Olefin cross-metathesis is a cornerstone reaction in organic synthesis where stereoselectivity is typically governed by the structure of the catalyst. In this work, we show that merging Grubbs second generation catalyst, a classical E-selective catalyst, with a readily available photocatalyst, enables the exclusive formation of the contra-thermodynamic Z-isomer. The scope and limitations of this unprecedented approach are discussed based on both computational and experimental mechanistic data.

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Catalyse
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hal-03838058 , version 1 (03-11-2022)

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Saïf Eddine Chérif, Avisek Ghosh, Saloua Chelli, Isabelle M Dixon, Jamil Kraiem, et al.. Merging Grubbs second-generation catalyst with photocatalysis enables Z-selective metathesis of olefins: scope, limitations, and mechanism. Chemical Science, 2022, 13, pp.12065 - 12070. ⟨10.1039/d2sc03961c⟩. ⟨hal-03838058⟩
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