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

Chemical Communications Pub Date: 2019-09-26 DOI: 10.1039/C9CC06505A

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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