Abstract
One-pot three-component Strecker reaction of ketones/fluorinated ketones for the preparation of α-aminonitriles/fluorinated α-aminonitriles has been achieved using trimethylsilyl trifluoromethanesulfonate [(CH3 )3 SiOSO2 CF3 , TMSOTf)] as a metal-free strong Lewis acid catalyst. These reactions are simple and clean, giving the products in high yield and high purity. α-Aminonitriles and their fluorinated analogues are important classes of compounds, which show interesting pharmaceutical and biological properties. Presence of fluorine atom increases their biological activities significantly.
Key words
multicomponent reaction - metal-free organocatalyst - TMSOTf - fluorinated ketones - α-aminonitriles
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General Procedure for the Strecker Reaction of Aldehydes and Ketones
2 Cl2 (5 mL) in a sealed pressure tube and the reaction mixture was stirred at r.t. for several hours. Completion of the reaction was monitored by NMR. After completion, the reaction mixture was quenched with H2 O and then extracted with CH2 Cl2 (3 × 15 mL). All the organic layers were collected, washed with brine solution, and dried over anhyd Na2 SO4 . Removal of the solvent under reduced pressure provided the crude products. The crude product was triturated with excess hexanes for several times and removal of the solvents under reduced pressure afforded the Strecker product (α-aminonitriles) in almost analytically pure form (by NMR). The products were characterized by analyzing their spectral data and comparing them with those of the authentic samples (see supporting information, which is available from the authors, and ref. 10).
