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A Rhodium‐Catalyzed Tandem Alkyne Dimerization/ 1,4‐Addition Reaction
Author(s) -
Lerum Ronald V.,
Russo Christopher M.,
Marquez Jocellie E.,
Chisholm John D.
Publication year - 2013
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.201300743
Subject(s) - rhodium , alkyne , chemistry , alkene , catalysis , methyl vinyl ketone , phosphine , ketone , coupling reaction , conjugated system , medicinal chemistry , ligand (biochemistry) , photochemistry , polymer chemistry , organic chemistry , combinatorial chemistry , biochemistry , receptor , polymer
A convenient three‐component coupling reaction for the construction of conjugated enynes using rhodium catalysis is reported. Dimerization of a monosubstituted alkyne followed by trapping of the vinyl metal intermediate with an electron‐deficient alkene, such as methyl vinyl ketone, provided moderate to good yields of these enynes. The use of the hindered electron‐rich tris( ortho ‐tolyl)phosphine as a ligand for the rhodium catalyst provided the best conversions to these complex products.