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Catalytic, transannular carbonyl-olefin metathesis reactions

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Abstract

Transannular carbonyl–olefin metathesis reactions complement existing procedures for related ring-closing, ring-opening, and intermolecular carbonyl-olefin metathesis. We herein report the development and mechanistic investigation of FeCl3-catalyzed transannular carbonyl-olefin metathesis reactions that proceed via a distinct reaction path compared to previously reported ring-closing and ring-opening protocols. Specifically, carbonyl-ene and carbonyl-olefin metathesis reaction pathways are competing under FeCl3-catalysis to ultimately favor metathesis as the thermodynamic product. Importantly, we show that distinct Lewis acid catalysts are able to distinguish between these pathways to enable the selective formation of either transannular carbonyl-ene or carbonyl-olefin metathesis products. These insights are expected to enable further advances in catalyst design to efficiently differentiate between these two competing reaction paths of carbonyl and olefin functionalities to further expand the synthetic generality of carbonyl-olefin metathesis.

Graphical abstract: Catalytic, transannular carbonyl-olefin metathesis reactions

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Publication details

The article was received on 28 Jul 2019, accepted on 19 Sep 2019 and first published on 25 Sep 2019


Article type: Edge Article
DOI: 10.1039/C9SC03716K
Chem. Sci., 2019, Advance Article
  • Open access: Creative Commons BY-NC license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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    Catalytic, transannular carbonyl-olefin metathesis reactions

    P. S. Riehl, D. J. Nasrallah and C. S. Schindler, Chem. Sci., 2019, Advance Article , DOI: 10.1039/C9SC03716K

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