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A Polystyrene‐Bound Triphenylphosphine Gold(I) Catalyst for the Glycosylation of Glycosyl ortho ‐Hexynylbenzoates
Author(s) -
Zhu Yugen,
Laval Stéphane,
Tang Yu,
Lian Gaoyan,
Yu Biao
Publication year - 2015
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201500276
Subject(s) - chemistry , phosphine , triphenylphosphine , catalysis , x ray photoelectron spectroscopy , polystyrene , leaching (pedology) , glycosyl , glycosylation , polymer chemistry , ligand (biochemistry) , heterogeneous catalysis , nuclear chemistry , organic chemistry , chemical engineering , polymer , environmental science , receptor , soil science , engineering , soil water , biochemistry
Abstract The efficacy of the heterogeneous polystyrene‐bound triphenylphosphine gold(I) catalyst 3 (PS‐[Ph 3 PAu I NTf 2 ]; PS=polystyrene; Tf=trifluoromethanesulfonyl) in the activation of glycosyl ortho ‐hexynylbenzoates for glycosylation is demonstrated. The shelf‐stable catalyst 3 (and its precursor 2 , PS‐[Ph 3 PAu I Cl]) were fully characterized by elemental analysis, X‐ray photoelectron spectroscopy (XPS), energy dispersive spectroscopy (EDS), and scanning electron microscopy (SEM), and showed remarkable catalytic activities and recyclability in glycosylation reactions as well as in the skeletal rearrangement of the 1,6‐enyne 4 . EDS analysis demonstrated that the phosphine ligand binds the gold strongly and prevents the leaching of the metal.