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Sulfoxonium and Sulfonium Ylides as Diazocarbonyl Equivalents in Metal‐Catalyzed Insertion Reactions
Author(s) -
Burtoloso Antonio C. B.,
Dias Rafael M. P.,
Leonarczyk Ives A.
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300581
Subject(s) - sulfonium , diazo , chemistry , carbene , intramolecular force , catalysis , insertion reaction , combinatorial chemistry , enantioselective synthesis , organic chemistry , salt (chemistry)
Since the pioneering contribution of Corey and Chaykovsky in 1965, sulfoxonium and sulfonium ylides have proven to be versatile intermediates in organic synthesis. One of their important applications, though not yet throughly investigated, is their substitution of diazocarbonyl compounds as safer carbene precursors. This microreview provides an overview and recent applications of sulfoxonium and sulfonium ylides in inter‐ and intramolecular metal‐catalyzed insertion reactions. It also plans to illustrate the promising synthetic utility of these stable carbene precursors in industry, mitigating potential safety problems generally encountered when the equivalent diazo compounds are employed. Moreover, it aims to inspire new contributions to this exciting growing area, especially in catalytic asymmetric reactions.