Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 137, Issue 22, Pages 7019-7022Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.5b02945
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Funding
- National Science Foundation [CHE-1058075, CHE-1261033]
- Research Council of Sweden
- Shenzhen Peacock Program [KQTD201103]
- AstraZeneca
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1058075] Funding Source: National Science Foundation
- Office Of The Director
- Office Of Internatl Science &Engineering [1261033] Funding Source: National Science Foundation
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A procedure for Ni-catalyzed cross-coupling of ketone enolates with alkenyl halides has been developed. Intermolecular coupling of aromatic and aliphatic ketone lithium enolates with a variety of alkenyl halides is achieved in the presence of Ni(cod)(2) catalyst (5 mol %), an N-heterocyclic carbene (NHC) ligand, and LiI (10 mol %) at 6-22 degrees C for 0.5-12 h with yields of up to 90%. During the initial development of this reaction, a misleading result with respect to the actual active catalyst was obtained using commercially available Q:Phos ligand, which was found to contain a trace of Pd metal contaminant sufficient to catalyze the reaction. However, under the final conditions optimized for Ni(cod)(2) in the presence of an NHC ligand, Pd was incompetent as a catalyst.
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