期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 131, 期 41, 页码 15032-15040出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja9055307
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资金
- Ministry of Education, Culture, Sports, Science and Technology, Japan
The synergetic effect of two Si-H groups leads to efficient reduction of carboxamides to amines by platinum catalysts under mild conditions The rate of the reaction is dependent on the distance of two Si-H groups, 1,1,3,3-tetramethyidisiloxane (TMDS) and 1,2-bis(dimethylsilyl)benzene are found to be an effective reducing reagent. The reduction of amides having other reducible functional groups such as NO2, CO2R, CN, C=C, Cl, and Br moieties proceeds with these groups remaining intact, providing a reliable method for the access to functionalized amine derivatives. The platinum-catalyzed reduction of amides with polymethylhydrosiloxane (PMHS) also proceeds under mild conditions. The reaction is accompanied by automatic removal of both platinum and silicon wastes as insoluble silicone resin, and the product is obtained by simple extraction. A mechanism involving double oxidative addition of TMDS to a platinum center is discussed.
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