Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 351, Issue 10, Pages 1637-1647Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200900085
Keywords
allylation; allylic alcohols; phenols; phosphines; ruthenium
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Funding
- Technology Foundation STW
- Council for the Chemical Sciences of the Netherlands Organization for Scientific Research (CW-NWO)
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A new catalytic method has been investigated to obtain either O- or C-allylated phenolic products using allyl alcohol or diallyl ether as the allyl donor. With the use of new cationic ruthenium(II) complexes as catalyst, both reactions can be performed with good selectivity. Active cationic Ru(II) complexes, having cyclopentadienyl and bidentate phosphine ligands are generated from the corresponding Ru(II) chloride complexes with a silver salt. The structures of three novel (diphosphine)Ru(II)CpCl catalyst precursor complexes are reported. It appears that the structure of the bidentate ligand has a major influence on catalytic activity as well as chemoselectivity. In addition, a strong, co-catalytic effect of small amounts of acid is revealed. Model experiments are described that have been used to build a reaction network that explains the origin and evolution in time of both O-allylated and C-allylated phenolic products. Some mechanistic implications of the observed Structure VS. performance relation of the [(diphosphine)RuCp](+) complexes and the cocatalytic role of added protons are discussed.
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