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Issue 91, 2019
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Catalytic selective mono- and difluoroalkylation using fluorinated silyl enol ethers

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Abstract

The judicious incorporation of a fluoroalkyl moiety often brings about beneficial effects on the properties of bioactive molecules. Consequently, efficient methods for selective fluoroalkylation are much sought after in drug discovery. Despite significant achievements in trifluoromethylation, selective mono- and difluoroalkylation is still undeveloped. Catalytic functionalization of fluorinated silyl enol ethers (FSEEs) emerges as a fruitful approach for the diversity-oriented synthesis of value-added α-mono or difluoroalkylated ketones. In this feature article, we detail our efforts in developing catalytic selective mono- and difluoroalkylation reactions using FSEEs. Specifically, we highlight our findings such as activating FSEEs by amines for catalytic enantioselective synthesis, taking advantage of the often observed high activity of FSEEs over the non-fluorinated analogues for reaction development, and the influence of C–F⋯H–X interactions on reactivity and selectivity.

Graphical abstract: Catalytic selective mono- and difluoroalkylation using fluorinated silyl enol ethers

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Publication details

The article was received on 30 Sep 2019, accepted on 21 Oct 2019 and first published on 21 Oct 2019


Article type: Feature Article
DOI: 10.1039/C9CC07677H
Chem. Commun., 2019,55, 13638-13648

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    Catalytic selective mono- and difluoroalkylation using fluorinated silyl enol ethers

    X. Hu, J. Yu and J. Zhou, Chem. Commun., 2019, 55, 13638
    DOI: 10.1039/C9CC07677H

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