Dalton Transactions (Print Edition) 2013-01-28

Palladium-catalyzed asymmetric Heck arylation of 2,3-dihydrofuran--effect of prolinate salts.

Adam Morel, Ewelina Silarska, Anna M Trzeciak, Juliusz Pernak

Index: Dalton Trans. 42(4) , 1215-22, (2013)

Full Text: HTML

Abstract

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.

Related Compounds

  • 2,3-DHF
  • iodoanisole

Related Articles:

An integrated microreactor system for self-optimization of a Heck reaction: from micro- to mesoscale flow systems.

2010-09-17

[Angew. Chem. Int. Ed. Engl. 49(39) , 7076-80, (2010)]

A gold(I)-catalyzed intramolecular reaction of propargylic/homopropargylic alcohols with oxirane.

2008-01-01

[Chemistry 14(23) , 7011-8, (2008)]

Short, enantioselective total synthesis of aflatoxin B2 using an asymmetric [3+2]-cycloaddition step.

2005-08-31

[J. Am. Chem. Soc. 127(34) , 11958-9, (2005)]

Phosphine-catalyzed domino reaction for the synthesis of conjugated 2,3-dihydrofurans from allenoates and Nazarov reagents.

2012-06-01

[Chem. Asian J. 7(7) , 1533-7, (2012)]

First successful application of diphosphite ligands in the asymmetric hydroformylation of dihydrofurans.

2005-03-07

[Chem. Commun. (Camb.) (9) , 1221-3, (2005)]

More Articles...