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Issue 47, 2018
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Rh(II)/phosphine-cocatalyzed synthesis of dithioketal derivatives from diazo compounds through simultaneous construction of two different C–S bonds

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Abstract

Rhodium(II)/phosphine-cocatalyzed bis-sulfuration of α-diazocarbonyl compounds using thiosulfonates as the sulfenylating agent, which provided two sulfur-containing moieties, was developed via simultaneous inter- and intra-molecular C–S bond formation. This novel protocol provides a rapid synthetic route to dithioketal derivatives in moderate to good yields in an atom-economic process. The transformation is proposed to proceed through phosphine ylide formation followed by S(O2)–S bond cleavage and rearrangement.

Graphical abstract: Rh(ii)/phosphine-cocatalyzed synthesis of dithioketal derivatives from diazo compounds through simultaneous construction of two different C–S bonds

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Publication details

The article was received on 28 Feb 2018, accepted on 10 Apr 2018 and first published on 11 Apr 2018


Article type: Communication
DOI: 10.1039/C8CC01656A
Citation: Chem. Commun., 2018,54, 5964-5967
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    Rh(II)/phosphine-cocatalyzed synthesis of dithioketal derivatives from diazo compounds through simultaneous construction of two different C–S bonds

    C. Rao, S. Mai and Q. Song, Chem. Commun., 2018, 54, 5964
    DOI: 10.1039/C8CC01656A

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