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Issue 8, 2011
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Organic reactions mediated by electrochemically generated ArS+

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Abstract

Low-temperature electrochemical oxidation of ArSSAr was carried out to generate a pool of “ArS+”. Spectroscopic studies (1H NMR and CSI-MS) of the resulting solution revealed the accumulation of ArS(ArSSAr)+. The resulting “ArS+” pool reacted with alkenes and alkynes to give diarylthio-substituted products. The “ArS+” pool rapidly reacted with thioacetals to give the corresponding alkoxycarbenium ion pools, which reacted with various carbon nucleophiles (indirect cation pool method). The reaction of the alkoxycarbenium ion pools with stilbene derivatives in the presence of ArSSAr gave thiochroman derivatives. In addition to such stoichiometric reactions, a catalytic amount of “ArS+” serves as an initiator and a chain carrier of some cationic chain reactions involving intramolecular carboncarbon bond formation. In situ generation of “ArS+” by electrochemical oxidation of ArSSAr with a catalytic amount of electricity in the presence of a substrate is also effective for such cationic chain reactions.

Graphical abstract: Organic reactions mediated by electrochemically generated ArS+

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Publication details

The article was received on 23 Nov 2010, accepted on 14 Jan 2011 and first published on 25 Feb 2011


Article type: Perspective
DOI: 10.1039/C0OB01070G
Org. Biomol. Chem., 2011,9, 2586-2596

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    Organic reactions mediated by electrochemically generated ArS+

    K. Matsumoto, S. Suga and J. Yoshida, Org. Biomol. Chem., 2011, 9, 2586
    DOI: 10.1039/C0OB01070G

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