Pd(II) complexes of monodentate deoxycholic acid derived binaphthyl diamido phosphites as chiral catalysts in the asymmetric Suzuki-Miyaura cross-coupling

[Display omitted] Chiral binaphthyl diamidophosphites derived from deoxycholic acid were synthesized and used as ligands for the preparation of mononuclear Pd(II) complexes, which were employed as catalysts in the asymmetric Suzuki-Miyaura cross-coupling of arylboronic acids with aryl bromides. Amon...

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Bibliographic Details
Published inTetrahedron: asymmetry Vol. 28; no. 11; pp. 1618 - 1625
Main Authors Iannucci, Grazia, Passarelli, Vincenzo, Passera, Alessandro, Iuliano, Anna
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 15.11.2017
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
HYDROGENATION
ENANTIOPURE BIS(DIAMIDOPHOSPHITE) LIGANDS
ENANTIOSELECTIVE SYNTHESIS
DIAMIDOPHOSPHITES
STEREOCHEMICAL CHARACTERIZATION
BIPHENYLPHOSPHITES
ALLYLIC SUBSTITUTION
ARYLBORONIC ACIDS
METAL-COMPLEXES
CONJUGATE ADDITION
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Summary:[Display omitted] Chiral binaphthyl diamidophosphites derived from deoxycholic acid were synthesized and used as ligands for the preparation of mononuclear Pd(II) complexes, which were employed as catalysts in the asymmetric Suzuki-Miyaura cross-coupling of arylboronic acids with aryl bromides. Among the different reaction parameters, the substrate concentration emerged as being crucial for the outcome of the reaction: the reaction was faster in a concentrated reaction mixture, and could be performed at 0°C, where the reaction promoted by the Pd-complexes was more enantioselective affording cross-coupling products with ee up to 70%.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2017.09.012