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Three Coordinated Organoaluminum Cation for Rapid and Selective Cyanosilylation of Carbonyls under Solvent‐Free Conditions
Author(s) -
Rawat Sandeep,
Bhandari Mamta,
Prashanth Billa,
Singh Sanjay
Publication year - 2020
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.202000309
Subject(s) - chemistry , cationic polymerization , nucleophile , adduct , catalysis , medicinal chemistry , lewis acids and bases , silane , nucleophilic addition , solvent , organic chemistry , polymer chemistry
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.