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1.
J Org Chem ; 89(13): 9440-9449, 2024 Jul 05.
Article in English | MEDLINE | ID: mdl-38875179

ABSTRACT

A mild protocol for electrochemically oxidative fluorodifunctionalization of styrenes has been demonstrated. The reaction proceeds under metal, external oxidant, and catalyst free conditions, allowing tunable access to a wide variety of synthetically useful fluoroalkyl derivatives, such as ß-fluorosulfone/fluoromethyl, fluorothiocyanation, and vinylsulfonyl derivatives. Moreover, CsF was shown to be the proper fluorine source for this electrochemical fluorodifunctionalization transformation.

2.
Org Lett ; 26(1): 241-246, 2024 Jan 12.
Article in English | MEDLINE | ID: mdl-38156980

ABSTRACT

Using easily handled CsF as a fluorine source, an electrochemically metal-free protocol for chemo- and regioselective synthesis of various types of long-chain perfluoroalkyl aromatics with gem-difluoroalkene as a substrate and an alcohol or azole as an additional nucleophile was developed. The eletrochemical transformation could tolerate several functional groups, such as halogens, cyanos, benzyls, and heterocycles, and is amenable to gram-scale. The application of this electrochemical method in radiofluorination was also tested.

3.
Org Lett ; 25(18): 3308-3313, 2023 May 12.
Article in English | MEDLINE | ID: mdl-37129411

ABSTRACT

A scalable electrochemical difunctionalization of gem-difluoroalkenes to structurally versatile difluoro motifs was achieved. This methodology features reagent-free conditions, good functional group tolerance, and a relatively broad substrate scope. Meanwhile, the electrolysis protocol is easy to handle, and the products show good regio- and chemoselectivity. The reaction mechanism was also preliminarily studied.

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