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Bailey GA, Fogg DE. Acrylate metathesis via the second-generation Grubbs catalyst: unexpected pathways enabled by a PCy3-generated enolate. J Am Chem Soc. 2015;137(23):7318-21doi: 10.1021/jacs.5b04524.
Bailey, G. A., & Fogg, D. E. (2015). Acrylate metathesis via the second-generation Grubbs catalyst: unexpected pathways enabled by a PCy3-generated enolate. Journal of the American Chemical Society, 137(23), 7318-21. https://doi.org/10.1021/jacs.5b04524
Bailey, Gwendolyn A, and Fogg, Deryn E. "Acrylate metathesis via the second-generation Grubbs catalyst: unexpected pathways enabled by a PCy3-generated enolate." Journal of the American Chemical Society vol. 137,23 (2015): 7318-21. doi: https://doi.org/10.1021/jacs.5b04524
Bailey GA, Fogg DE. Acrylate metathesis via the second-generation Grubbs catalyst: unexpected pathways enabled by a PCy3-generated enolate. J Am Chem Soc. 2015 Jun 17;137(23):7318-21. doi: 10.1021/jacs.5b04524. Epub 2015 Jun 05. PMID: 26030596.
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J Am Chem Soc. 2015 Jun 17;137(23):7318-21. doi: 10.1021/jacs.5b04524. Epub 2015 Jun 05.

Acrylate metathesis via the second-generation Grubbs catalyst: unexpected pathways enabled by a PCy3-generated enolate.

Journal of the American Chemical Society

Gwendolyn A Bailey, Deryn E Fogg

Affiliations

  1. Center for Catalysis Research and Innovation and Department of Chemistry, University of Ottawa, Ottawa, Ontario K1N6N5 Canada.

PMID: 26030596 DOI: 10.1021/jacs.5b04524

Abstract

The diverse applications of acrylate metathesis range from synthesis of high-value α,β-unsaturated esters to depolymerization of unsaturated polymers. Examined here are unexpected side reactions promoted by the important Grubbs catalyst GII. Evidence is presented for attack of PCy3 on the acrylate olefin to generate a reactive carbanion, which participates in multiple pathways, including further Michael addition, proton abstraction, and catalyst deactivation. Related chemistry may be anticipated whenever labile metal-phosphine complexes are used to catalyze reactions of substrates bearing an electron-deficient olefin.

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