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Oxidative Addition of α‐Glycosyl Halides to a Platinum(0) Olefin Complex: Stereochemistry of Pt−C Bond Formation
Author(s) -
Annunziata Alfonso,
Cucciolito Maria Elena,
Esposito Roberto,
Traboni Serena,
Tuzi Angela,
Budzelaar Peter H. M.,
Ruffo Francesco
Publication year - 2021
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.202001088
Subject(s) - chemistry , glycosyl , oxidative addition , diastereomer , halide , platinum , stereochemistry , olefin fiber , medicinal chemistry , catalysis , organic chemistry
The oxidative addition of α‐glucosyl and α‐galactosyl halides to the platinum(0) complex [Pt(2,9‐dimethyl‐1,10‐phenanthroline)(ethene)] has been investigated. In all cases the main reaction product is the five‐coordinate Pt(II) complex containing in axial position an α‐glycosyl fragment in the unusual 1 C 4 conformation. In the case of glucose, a minor product could be identified as the β isomer, which retains the typical 4 C 1 chair. The single crystal structures of two diastereomers are compared. The outcome of the reaction does not depend on the nature of the halide and is only slightly affected by the solvent. The addition mechanism is discussed, also in the light of literature data. Experimental data, along with DFT calculations, point towards a radical chain mechanism.