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Issue 4, 2013
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Palladium-catalyzed asymmetric Heck arylation of 2,3-dihydrofuran – effect of prolinate salts

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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.

Graphical abstract: Palladium-catalyzed asymmetric Heck arylation of 2,3-dihydrofuran – effect of prolinate salts

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Publication details

The article was received on 25 Jul 2012, accepted on 18 Oct 2012 and first published on 22 Oct 2012


Article type: Paper
DOI: 10.1039/C2DT31672B
Citation: Dalton Trans., 2013,42, 1215-1222
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    Palladium-catalyzed asymmetric Heck arylation of 2,3-dihydrofuran – effect of prolinate salts

    A. Morel, E. Silarska, A. M. Trzeciak and J. Pernak, Dalton Trans., 2013, 42, 1215
    DOI: 10.1039/C2DT31672B

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