131516-13-7Relevant articles and documents
Palladium-catalyzed asymmetric Heck arylation of 2,3-dihydrofuran-effect of prolinate salts
Morel, Adam,Silarska, Ewelina,Trzeciak, Anna M.,Pernak, Juliusz
, p. 1215 - 1222 (2013/02/23)
Chiral ionic liquids (CILs) containing l-prolinate and l-lactate anions and non-chiral quaternary ammonium cations were employed in the palladium catalyzed enantioselective Heck arylation of 2,3-dihydrofuran with aryl iodides (iodobenzene, 4-iodotoluene, 2-iodoanisole, 4-iodoanisole, 4-iodoacetophenone). In all the reactions 2-aryl-2,3-dihydrofuran (3) was obtained as the main product with the yield up to 52% at the total conversion reaching 83%. Product 3, 2-phenyl-2,3-dihydrofuran, was obtained with excellent enantioselectivity (>99% ee) in a 6 h reaction with tetrabutylammonium l-prolinate. In the proposed homogeneous reaction Pd(0) nanoparticles are considered as a resting state of the catalyst and a source of soluble palladium species catalyzing the Heck reaction. The yield and stereoselectivity of the Heck reaction are strongly influenced by the kind of non-chiral cations present in CILs. The Royal Society of Chemistry 2013.
Palladium-catalyzed asymmetric arylation of 2,3-dihydrofuran: 1,8-Bis(dimethylamino)naphthalene as an efficient base
Ozawa, Fumiyuki,Kubo, Akihiko,Hayashi, Tamio
, p. 1485 - 1488 (2007/10/02)
Reaction of 2,3-dihydrofuran with aryl triflate (1) in the presence of a base and a palladium catalyst, generated in situ from Pd(OAc)2 and (R)-BINAP, gave (R)-2-aryl-2,3-dihydrofuran (2) and a small amount of (S)-2-aryl-2,5-dihydrofuran (3). T