Glucosamine-based phosphines. Efficient ligands in the Suzuki cross-coupling reaction in water

Coupling of protected or non-protected d-glucosamine with o- or p-(diphenylphosphino)benzoic acid generates carbohydrate-substituted phosphines in quite good yields. The catalytic performance of these new neutral ligands is demonstrated in the Suzuki cross-coupling reaction. The polyhydroxy phosphin...

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Bibliographic Details
Published inTetrahedron letters Vol. 43; no. 41; pp. 7397 - 7400
Main Authors Parisot, Sophie, Kolodziuk, Robert, Goux-Henry, Catherine, Iourtchenko, Alexander, Sinou, Denis
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 07.10.2002
Elsevier
Subjects
carbohydrate
Chemistry
Chemistry, Organic
Physical Sciences
recycling
Science & Technology
Suzuki coupling
water-soluble
Suzuki coupling
recycling
carbohydrate
water-soluble
2-PHASE CATALYSIS
AQUEOUS-MEDIA
ARYLBORONIC ACIDS
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Summary:Coupling of protected or non-protected d-glucosamine with o- or p-(diphenylphosphino)benzoic acid generates carbohydrate-substituted phosphines in quite good yields. The catalytic performance of these new neutral ligands is demonstrated in the Suzuki cross-coupling reaction. The polyhydroxy phosphines are more active than the peracetylated phosphines, and the process tolerates electron-rich as well as electron-poor substituents. Excellent turnovers are observed, and the catalyst can be recycled. Glucosamine-based phosphines efficiently catalyzed the Suzuki reaction in water, the recycling of the catalyst being possible.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(02)01749-5