Three Coordinated Organoaluminum Cation for Rapid and Selective Cyanosilylation of Carbonyls under Solvent‐Free Conditions
Sandeep Rawat, Mamta Bhandari, Billa Prashanth, Sanjay Singh
Abstract
Abstract The well‐defined three coordinated electronically unsaturated cationic organoaluminum complex [({(2,6‐ i Pr 2 C 6 H 3 N)P(Ph 2 )} 2 N)AlMe] + [MeB(C 6 F 5 ) 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.