Palladium Catalyzed Oxidative Coupling of α-Enolic Dithioesters: A New Entry to 3,4,5-Trisubstituted 1,2-Dithioles via a Double Activation Strategy

Chowdhury, Sushobhan ; Chanda, Tanmoy ; Koley, Suvajit ; Ramulu, B. Janaki ; Jones, Raymond C. F. ; Singh, Maya Shankar (2013) Palladium Catalyzed Oxidative Coupling of α-Enolic Dithioesters: A New Entry to 3,4,5-Trisubstituted 1,2-Dithioles via a Double Activation Strategy Organic Letters, 15 (20). pp. 5386-5389. ISSN 1523-7060

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Official URL: http://doi.org/10.1021/ol402728y

Related URL: http://dx.doi.org/10.1021/ol402728y

Abstract

An operationally simple, facile, and convenient one-pot straightforward method for the construction of 3,4,5-trisubstituted 1,2-dithioles has been explored and developed via palladium catalyzed self-coupling of α-enolic dithioesters for the first time. Pd(0) efficiently catalyzes the activation and cleavage of S–H and C–S bonds to achieve cascade coupling, which results in the concomitant formation of new S–S and C–C bonds. Optimization data, substrate scope, and mechanistic insights are discussed

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