Tetraarylphosphonium salts as soluble supports for oxidative catalysts and reagents.
Tetraarylphosphonium (TAP)-supported DMSO, TEMPO, and DIB reagents were synthesized and used for the oxidation of alcohols, including Swern oxidation and for the alpha-acetoxylation of ketones. By taking advantage of the predictable solubility properties of the TAP unit, simple precipitation and filtration of the phosphonium moiety permit complete separation of the desired oxidation products. This paper describes the preparation of these three TAP-supported oxidative reagents and their activity in the aforementioned oxidative transformations. Furthermore, we have demonstrated that these reagents can be recycled directly when used in catalytic processes and following regeneration when used in stoichiometric processes.
Département de chimie, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, Québec, Canada H3C 3J7.
Marie-Noelle
MN
Roy
Jean-Christophe
JC
Poupon
André B
AB
Charette
D000438:Alcohols / Q000737:chemistry; D002384:Catalysis; D003497:Cyclic N-Oxides / Q000737:chemistry*; D004121:Dimethyl Sulfoxide / Q000737:chemistry*; D007202:Indicators and Reagents / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D010084:Oxidation-Reduction; D012492:Salts / Q000138:chemical synthesis / Q000737:chemistry; D012995:Solubility; D013237:Stereoisomerism
D000438:Alcohols; D003497:Cyclic N-Oxides; D007202:Indicators and Reagents; D007659:Ketones; D009943:Organophosphorus Compounds; D012492:Salts; C003959:TEMPO; D004121:Dimethyl Sulfoxide