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Palladium-catalyzed tandem cyclization/sulfonylation of homoallenyl amides with sodium sulfinates

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Abstract

A palladium-catalyzed cyclizative sulfonylation of homoallenyl amides using sodium sulfinates as the sulfonylation reagent and PhI(O2CCF3)2 as the oxidant has been realized. The reaction proceeds at room temperature and produces structurally diverse 2-amino-5-sulfonylmethylfurans in good to excellent yields. A Pd(II)/Pd(IV) catalytic cycle has been proposed for the formation of sulfonylated furans. The concurrent formation of a furan moiety and a C(sp3)–sulfur bond in a single operation makes it a very attractive method for organic synthesis.

Graphical abstract: Palladium-catalyzed tandem cyclization/sulfonylation of homoallenyl amides with sodium sulfinates

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Publication details

The article was received on 02 Aug 2017, accepted on 11 Aug 2017 and first published on 11 Aug 2017


Article type: Paper
DOI: 10.1039/C7OB01922J
Citation: Org. Biomol. Chem., 2017, Advance Article
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    Palladium-catalyzed tandem cyclization/sulfonylation of homoallenyl amides with sodium sulfinates

    Y. Wan, J. Zhang, Y. Chen, L. Kong, F. Luo and G. Zhu, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB01922J

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