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Synthesis of α-arylthioacetones using TEMPO as the C3 synthon via a reaction cascade of sequential oxidation, skeletal rearrangement and C–S bond formation

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Abstract

Here, we present an unprecedented pathway to α-sulfenylated carbonyl compounds from commercially available thiols and universally employed TEMPO and its analogues, which act as C3 synthons through skeletal rearrangement under simple and metal-free conditions. Mechanism studies suggest that this reaction involves a consecutive radical oxidation and cation coupling process. TEMPO analogues and thiols serve as oxidants and reductive reagents, respectively, along the radical process, while in the coupling process, the former ones afford C3 synthons to couple with related sulfur sources.

Graphical abstract: Synthesis of α-arylthioacetones using TEMPO as the C3 synthon via a reaction cascade of sequential oxidation, skeletal rearrangement and C–S bond formation

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Publication details

The article was received on 04 Jan 2019, accepted on 06 Feb 2019 and first published on 06 Feb 2019


Article type: Communication
DOI: 10.1039/C9OB00018F
Citation: Org. Biomol. Chem., 2019, Advance Article

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    Synthesis of α-arylthioacetones using TEMPO as the C3 synthon via a reaction cascade of sequential oxidation, skeletal rearrangement and C–S bond formation

    J. Zou, Y. Jiang, S. Lei, G. Yin, X. Hu, Q. Zhao and Z. Wang, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C9OB00018F

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