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Nucleophilic ortho ‐Propargylation of Aryl Sulfoxides: An Interrupted Pummerer/Allenyl Thio‐Claisen Rearrangement Sequence
Author(s) -
Eberhart Andrew J.,
Procter David J.
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201300223
Subject(s) - nucleophile , intramolecular force , aryl , thio , propargyl , claisen rearrangement , computer science , combinatorial chemistry , chemistry , sulfur , medicinal chemistry , stereochemistry , organic chemistry , alkyl , catalysis
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.