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

• Published in: Journal of the American Chemical Society Vol. 133; no. 22; pp. 8482 - 8485
• Main Authors: He, Weimin, Li, Chaoqun, Zhang, Liming
• Format: Journal Article
• Language: English
• 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

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...