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Synthesis of polysubstituted cyclic 1,2-diketones enabled by iterative sulfoxide-mediated arylation

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Abstract

A metal-free α-C–H functionalization of cyclic 1,2-diketones with aryl sulfoxides has been developed. This regioselective arylation involves nucleophilic substitution at the activated sulfoxide with a diosphenol, followed by [3,3]-sigmatropic rearrangement. This protocol can also be applied to the synthesis of polysubstituted cyclic 1,2-diketones with predictable structures by iterative arylations.

Graphical abstract: Synthesis of polysubstituted cyclic 1,2-diketones enabled by iterative sulfoxide-mediated arylation

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Publication details

The article was received on 22 Aug 2019, accepted on 25 Sep 2019 and first published on 26 Sep 2019


Article type: Communication
DOI: 10.1039/C9CC06505A
Chem. Commun., 2019, Advance Article

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    Synthesis of polysubstituted cyclic 1,2-diketones enabled by iterative sulfoxide-mediated arylation

    X. Meng, D. Chen, X. Cao, J. Luo, F. Wang and S. Huang, Chem. Commun., 2019, Advance Article , DOI: 10.1039/C9CC06505A

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