Efficient Cycloisomerization of Propargyl Amides by Electrophilic Gold(I) Complexes of KITPHOS Monophosphines: A Comparative Study

Electrophilic gold(I) complexes of diphenyl- and dicyclohexylphosphino-based KITPHOS monophosphines catalyze the 5-exo-dig cycloisomerization of a range of propargyl amides to afford the corresponding alkylidene oxazolines; in all cases catalysts formed from diphenylphosphino-substituted KITPHOS mon...

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Published inOrganometallics Vol. 29; no. 18; pp. 4139 - 4147
Main Authors Doherty, Simon, Knight, Julian G, Hashmi, A. Stephen K, Smyth, Catherine H, Ward, Nicholas A. B, Robson, Katharine J, Tweedley, Sophie, Harrington, Ross W, Clegg, William
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 27.09.2010
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Physical Sciences
Science & Technology
OXAZOLE SYNTHESIS
COUPLING REACTIONS
CONTAINING CARBONYL YLIDES
CATALYZED C-C
SILVER
INTRAMOLECULAR HYDROAMINATION
PLATINUM
CRYSTAL-STRUCTURES
LIGAND
HIGHLY EFFICIENT
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Summary:Electrophilic gold(I) complexes of diphenyl- and dicyclohexylphosphino-based KITPHOS monophosphines catalyze the 5-exo-dig cycloisomerization of a range of propargyl amides to afford the corresponding alkylidene oxazolines; in all cases catalysts formed from diphenylphosphino-substituted KITPHOS monophosphines outperformed their dicyclohexylphosphino counterparts as well as that based on triphenylphosphine, an indication that the biaryl/biaryl-like framework may be responsible for imparting high catalyst efficiency.
ISSN:0276-7333
1520-6041
DOI:10.1021/om1006769