Three Coordinated Organoaluminum Cation for Rapid and Selective Cyanosilylation of Carbonyls under Solvent-Free Conditions
The well-defined three coordinated electronically unsaturated cationic organoaluminum complex [({(2,6-iPr2C6H3N)P(Ph2)}2N)AlMe]+[MeB(C6F5)3]? (1), has been utilized to catalyze the cyanosilylation of aldehydes and ketones under mild and solvent-free conditions. Moreover, catalyst 1 showed high chemoselective cyanosilylation of aldehydes over ketones, nitriles and olefins. The multinuclear NMR investigations revealed that cyanosilylation proceeds via Lewis adduct formation between 1 and TMSCN thereby activating TMSCN (Si-CN bond) followed by nucleophilic attack of the carbonyl oxygen at the Si center of the activated silane and formation of the product.
Synthesis of fluoroorganic O-(Trirnethylsilyl)cyanhydrines
Fluororganic and/or sterically hindered cyanohydrines are useful synthetic reagents, not readily available directly from e.g. aldehydes or ketones and hydrogen cyanide. By using trimethylsilyl cyanide (TMSCN), the obtained O-Silyl-cyanohydrines can be app
Sander, Michael,Sundermeyer, Wolfgang
p. 296 - 306
(2007/10/03)
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