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

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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… Click to show full abstract

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.

Keywords: scope limitations; second generation; catalyst; generation catalyst; grubbs second; merging grubbs

Journal Title: Chemical Science
Year Published: 2022

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