期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 133, 期 22, 页码 8482-8485出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja2029188
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资金
- NSF [CHE-0969157]
- Amgen
- UCSB
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [0969157] Funding Source: National Science Foundation
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 % BrettPhos-AuNTf2 as the catalyst.
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