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First Application of Secondary Phosphines as Supporting Ligands for the Palladium‐Catalyzed Heck Reaction: Efficient Activation of Aryl Chlorides
Author(s) -
Schnyder Anita,
Aemmer Thomas,
Indolese Adriano F.,
Pittelkow Ulrich,
Studer Martin
Publication year - 2002
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 - 10.1002/1615-4169(200207)344:5<495::aid-adsc495>3.0.co;2-6
Subject(s) - chemistry , aryl , palladium , heck reaction , catalysis , styrene , vinyl ether , acrylate , organic chemistry , ethylene , medicinal chemistry , reactivity (psychology) , combinatorial chemistry , polymer chemistry , copolymer , alkyl , medicine , polymer , alternative medicine , pathology
Secondary dialkylphosphines were successfully used for the first time as efficient supporting ligands for the palladium‐catalyzed Heck reaction of electron‐rich and electron‐poor aryl chlorides with olefins such as acrylate, ethylene, styrene, and n ‐butyl vinyl ether. The yields with HP( t ‐butyl) 2 and HP(adamantyl) 2 were comparable or better than those obtained with known systems of tertiary phosphines such as P(cyclohexyl) 3 and P( t ‐butyl) 3 , especially at a catalyst loading of <1 mol %. In comparison with tertiary phosphines, the secondary phosphines have the advantage of being readily available at low cost on a technical scale, and are comparable with respect to handling and oxygen sensitivity.