Premium
Catalytic Propargylic Substitution Reactions
Author(s) -
Miyake Yoshihiro,
Uemura Sakae,
Nishibayashi Yoshiaki
Publication year - 2009
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.200900214
Subject(s) - heteroatom , catalysis , chemistry , substitution reaction , nucleophile , allylic rearrangement , enantioselective synthesis , nucleophilic substitution , transition metal , combinatorial chemistry , organic chemistry , ring (chemistry)
In sharp contrast to the well‐established transition metal‐ catalyzed allylic substitution reactions, the study of the corresponding propargylic substitution reactions has been quite limited for constructing carbon–carbon and carbon–heteroatom bonds at the propargylic position. However, during the last decade, general and useful catalytic reactions have been developed extensively. In this Review, we summarize recent advances in catalytic propargylic substitution reactions of propargylic alcohols and their derivatives with heteroatom‐ and carbon‐centered nucleophiles. In addition to a variety of transition metals, such as Ru, Re, Rh, Ir, Ni, Pd, Pt, and Cu, which form organometallic species as intermediates, several Lewis acids and Brønsted acids are also applicable as catalysts in these reactions. The reaction mechanism and the scope of nucleophiles that can be used depend on the nature of the catalysts. Some examples of enantioselective substitution reactions at the propargylic position are also described.