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Direct access to α-sulfenylated amides/esters via sequential oxidative sulfenylation and C–C bond cleavage of 3-oxobutyric amides/esters

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Abstract

An efficient, environmentally benign and unprecedented synthesis of various α-sulfenylated amides/esters has been developed under oxygen atmosphere. The reaction shows good functional group tolerance and excellent chemo/regioselectivity. All the desired products were obtained in moderate to excellent yields, even on the gram scale. Practically, the related α-thiol Weinreb amide can be readily transferred to a series of prospective compounds, and selenium atom can be introduced to the α-sites of the amides in high yields.

Graphical abstract: Direct access to α-sulfenylated amides/esters via sequential oxidative sulfenylation and C–C bond cleavage of 3-oxobutyric amides/esters

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Publication details

The article was received on 24 Nov 2017, accepted on 15 Dec 2017 and first published on 15 Dec 2017


Article type: Communication
DOI: 10.1039/C7CC09026A
Citation: Chem. Commun., 2018, Advance Article
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    Direct access to α-sulfenylated amides/esters via sequential oxidative sulfenylation and C–C bond cleavage of 3-oxobutyric amides/esters

    Y. Jiang, J. Deng, H. Wang, J. Zou, Y. Wang, J. Chen, L. Zhu, H. Zhang, X. Peng and Z. Wang, Chem. Commun., 2018, Advance Article , DOI: 10.1039/C7CC09026A

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