An Efficient [2 + 2 + 1] Synthesis of 2,5-Disubstituted Oxazoles via Gold-Catalyzed Intermolecular Alkyne Oxidation

The first efficient intermolecular reaction of gold carbene intermediates generated via gold-catalyzed alkyne oxidation has been realized using nitriles as both the reacting partner and the reaction solvent, offering a generally efficient synthesis of 2,5-disubstituted oxazoles with broad substrate...

Full description

Saved in:
Bibliographic Details
Published inJournal of the American Chemical Society Vol. 133; no. 22; pp. 8482 - 8485
Main Authors He, Weimin, Li, Chaoqun, Zhang, Liming
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 08.06.2011
Amer Chemical Soc
Subjects
Alkynes - chemistry
Catalysis
Chemistry
Chemistry, Multidisciplinary
Gold - chemistry
Molecular Structure
Oxazoles - chemical synthesis
Oxazoles - chemistry
Oxidation-Reduction
Physical Sciences
Science & Technology
KETONES
ACTIVATION
ONE-POT SYNTHESIS
COUPLING REACTIONS
NITRILES
MEDIATED SYNTHESIS
TRIFLUOROMETHANESULFONATE
CASCADE
CYCLOISOMERIZATION
CYCLIZATION
Online AccessGet full text

Cover

More Information
Summary:The first efficient intermolecular reaction of gold carbene intermediates generated via gold-catalyzed alkyne oxidation has been realized using nitriles as both the reacting partner and the reaction solvent, offering a generally efficient synthesis of 2,5-disubstituted oxazoles with broad substrate scope. The overall reaction is a [2 + 2 + 1] annulation of a terminal alkyne, a nitrile, and an oxygen atom from an oxidant. The reaction conditions are exceptionally mild, and a range of functional groups are easily tolerated. With complex and/or expensive nitriles, only 3 equiv could be sufficient to achieve serviceable yields in the absence of any solvent and using only 1 mol % BrettPhosAuNTf2 as the catalyst.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja2029188