Transition-Metal-Catalyzed Chemoselective Methylenation of Dicarbonyl Substrates

Transition-Metal-Catalyzed Chemoselective Methylenation of Dicarbonyl Substrates

Rhodium- and copper-catalyzed methylenation reactions with trimethylsilyldiazomethane, triphenylphosphine, and 2-propanol were used to react chemoselectively with aldehydes, alkoxymethylketones, and trifluoromethylketones in substrates also containing a less reactive carbonyl group. Terminal alkenes...

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Veröffentlicht in:Journal of organic chemistry 2008-09, Vol.73 (17), p.6828-6830
Hauptverfasser: Lebel, Hélène, Davi, Michaël, Stokłosa, Grzegorz T
Format: Artikel
Sprache:eng
Schlagworte:
2-Propanol - chemistry
Aldehydes - chemistry
Catalysis
Catalytic reactions
Chemistry
Copper - chemistry
Diazomethane - analogs & derivatives
Diazomethane - chemistry
Exact sciences and technology
General and physical chemistry
Ketones - chemistry
Methylation
Models, Chemical
Organophosphorus Compounds - chemistry
Rhodium - chemistry
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
Transition Elements - chemistry
Trimethylsilyl Compounds - chemistry
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Beschreibung
Zusammenfassung:Rhodium- and copper-catalyzed methylenation reactions with trimethylsilyldiazomethane, triphenylphosphine, and 2-propanol were used to react chemoselectively with aldehydes, alkoxymethylketones, and trifluoromethylketones in substrates also containing a less reactive carbonyl group. Terminal alkenes were obtained in high yields, and no protecting group was necessary in the methylenation process.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo800777w