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A New Highly Active Diphosphane‐Palladium(II) Complex as a Catalyst Precursor for the Heck Reaction
Author(s) -
Sjövall Sven,
Johansson Maria H.,
Andersson Carlaxel
Publication year - 2003
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.200390051
Subject(s) - chemistry , iodobenzene , cyclohexane , heck reaction , palladium , ligand (biochemistry) , catalysis , methyl acrylate , yield (engineering) , medicinal chemistry , stereochemistry , organic chemistry , biochemistry , polymer , receptor , materials science , copolymer , metallurgy
The new diphosphane ligand cis ‐1,3‐bis[(diphenylphosphanyl)methyl]cyclohexane ( 4 ) has been prepared and has allowed the synthesis of the palladium complex cis ‐[Pd( 4 )(CO 2 CF 3 ) 2 ] ( 6 ). To obtain cis complexation of the diphosphane in 6 the cyclohexane skeleton adopts a chair conformation with a diaxial orientation of the substituents, a structure that has been verified by an X‐ray structure determination. This complex efficiently catalyses the vinylation of iodo‐ and bromobenzenes in high yields. For the best reaction, with methyl acrylate and iodobenzene, a yield of >98% was obtained with an average turnover frequency of 11 760 h −1 and a turnover number of 1 176 000.