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Issue 12, 2016
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Bromomethyllithium-mediated chemoselective homologation of disulfides to dithioacetals

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Abstract

An efficient, chemoselective homologation of disulfides and diselenides to the corresponding dithio- and diselenoacetals has been developed via the addition of bromomethyllithium. Chemoselectivity is fully preserved in the presence of concomitant electrophilic sites decorating the substrates. The synthetic potential of selected dithioacetals has been evaluated in Feringa–Fañanas-Mastral-type Pd-catalyzed coupling with an organolithium and in the unusual 1,4-addition to a Weinreb amide.

Graphical abstract: Bromomethyllithium-mediated chemoselective homologation of disulfides to dithioacetals

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Publication details

The article was received on 14 Dec 2015, accepted on 30 Dec 2015 and first published on 04 Jan 2016


Article type: Communication
DOI: 10.1039/C5CC10280D
Citation: Chem. Commun., 2016,52, 2639-2642
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    Bromomethyllithium-mediated chemoselective homologation of disulfides to dithioacetals

    V. Pace, A. Pelosi, D. Antermite, O. Rosati, M. Curini and W. Holzer, Chem. Commun., 2016, 52, 2639
    DOI: 10.1039/C5CC10280D

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