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J Am Chem Soc. 2013 May 15;135(19):7312-23. doi: 10.1021/ja4017683. Epub 2013 May 3.

Sulfur(IV)-mediated transformations: from ylide transfer to metal-free arylation of carbonyl compounds.

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1
Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany.

Abstract

The development of a direct ylide transfer to carbonyl derivatives and of a sulfoxide-mediated arylation is presented from a unified perspective. Mechanistic studies (including density functional calculations) support a common reaction pathway and showcase how subtle changes in reactant properties can lead to disparate and seemingly unrelated reaction outcomes.

PMID:
23641807
DOI:
10.1021/ja4017683
[Indexed for MEDLINE]
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