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Iridium Complex‐Catalyzed Cross‐Coupling Reaction of Terminal Alkynes with Internal Alkynes via CH Activation of Terminal Alkynes
Author(s) -
Hirabayashi Tomotaka,
Sakaguchi Satoshi,
Ishii Yasutaka
Publication year - 2005
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200404359
Subject(s) - alkyne , chemistry , iridium , catalysis , terminal (telecommunication) , adduct , coupling reaction , ligand (biochemistry) , medicinal chemistry , combinatorial chemistry , stereochemistry , organic chemistry , telecommunications , biochemistry , receptor , computer science
The cross‐dimerization of an electron‐rich terminal alkyne with an electron‐deficient internal alkyne was promoted by an iridium complex to produce a 1 : 1 adduct in high regio‐ and stereoselectivities. This reaction was extended to various combinations of terminal alkynes with internal alkynes such as alkynyl esters and alkynyl aldehydes. The selectivity of the reaction was found to markedly depend on the ligands used. When dppe was used as a ligand, the 1 : 2 cross‐cyclotrimerization reaction took place to form substituted benzene derivatives. A plausible reaction path was suggested based on a labeling experiment. This reaction provides a method for the production of complicated enynes which are difficult to be prepared by conventional methods.