fulltext.study @t Gmail

Effect of chiral ionic liquids on palladium-catalyzed Heck arylation of 2,3-dihydrofuran

Paper ID Volume ID Publish Year Pages File Format Full-Text
41069 45876 2011 8 PDF Available
Title
Effect of chiral ionic liquids on palladium-catalyzed Heck arylation of 2,3-dihydrofuran
Abstract

It is demonstrated that a relatively small amount of IL (IL = ionic liquid) can dramatically affect conversion in the Heck arylation of 2,3-dihydrofuran with iodobenzene, catalyzed by Pd(OAc)2 in DMF as a solvent. In all reactions, 2-phenyl-2,3-dihydrofuran (3) was obtained as the main product, and conversion increased even up to 10 times when pyridinium salts with 1-butyl-4-methylpyridinium cation were applied. In a 1:1 mixture of DMF and H2O as solvent, the addition of ILs led to a remarkable deactivation of the catalyst, and this effect was most visible in the presence of imidazolium salts containing a 1-butyl-3-methylimidazolium cation. The influence of the anionic part of ILs on the reaction course was tested using a series of morpholinium salts and, depending on the anion, conversion varied from 0.4% to even 100%. When morpholinium salts with chiral anions were used, e.e. values of up to 10% were obtained, which is the highest value for the Heck reaction involving IL as a chirality source.

Graphical abstractFigure optionsDownload full-size imageDownload high-quality image (93 K)Download as PowerPoint slideHighlights► Heck arylation of 2,3-dihydrofuran catalyzed by phosphorus-free palladium catalyst. ► The promoting effect of pyridinium ILs on the yield of the cross-coupling product. ► Application of new chiral ILs as co-catalyst in the Heck reaction. ► Effect of anionic part of ILs on the yield of the Heck reaction.

Keywords
Homogeneous catalysis; Palladium; Heck reaction; Asymmetric catalysis; Ionic liquids
First Page Preview
Effect of chiral ionic liquids on palladium-catalyzed Heck arylation of 2,3-dihydrofuran
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us
Publisher
Database: Elsevier - ScienceDirect
Journal: Applied Catalysis A: General - Volumes 409–410, 15 December 2011, Pages 148–155
Authors
, , , ,
Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us