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

Chem Sci. 2022 Sep 22;13(41):12065-12070. doi: 10.1039/d2sc03961c. eCollection 2022 Oct 26.

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.

PMID:36349104 | PMC:PMC9600307 | DOI:10.1039/d2sc03961c

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