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Andrew J. Eberhart and Prof. David J. Procter Nucleophilic ortho-Propargylation of Aryl Sulfoxides: An Interrupted Pummerer/Allenyl Thio-Claisen Rearrangement Sequence Angewandte Chemie International Edition 52

Version of Record online: 27 FEB 2013 | DOI: 10.1002/anie.201300223

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A new direction: The nucleophilic ortho-propargylation of aryl sulfoxides exploits intermolecular delivery of the nucleophile to sulfur followed by an intramolecular relay to carbon (see scheme). The simple, metal-free procedure is general, regiospecific with regard to the propargyl nucleophile, and completely selective for products of ortho-propargylation over allenylation.

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