Organic Letters
Organic Letters
5 years ago

Redox-Neutral Access to Sultams from 2-Nitrochalcones and Sulfur with Complete Atom Economy

Redox-Neutral Access to Sultams from 2-Nitrochalcones and Sulfur with Complete Atom Economy
Pascal Retailleau, Thanh Binh Nguyen
A catalyst-free, redox-neutral, and completely atom-economical synthesis of sultams by simply heating 2-nitrochalcones with elemental sulfur in 3-picoline or N-methylmorpholine is described. The S–N, C–S, and S═O bonds of the sulfonamide are efficiently formed between the nitrogen atom of the 2-nitro group and the α-carbon of the chalcones and elemental sulfur with the migration of two oxygen atoms from the 2-nitro group to the sulfur atom.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01766

DOI: 10.1021/acs.orglett.7b01766

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