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Volumn , Issue 15, 2007, Pages 2395-2399

Trimethylsilyl trifluoromethanesulfonate as a metal-free, homogeneous and strong lewis acid catalyst for efficient one-pot synthesis of α-aminonitriles and their fluorinated analogues

Author keywords

aminonitriles; Fluorinated ketones; Metal free organocatalyst; Multicomponent reaction; TMSOTF

Indexed keywords

AMINONITRILE; KETONE; LEWIS ACID; TRIFLUOROMETHANESULFONIC ACID TRIMETHYLSILYL ESTER; TRIMETHYLSILYL DERIVATIVE; UNCLASSIFIED DRUG;

EID: 34948892808     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-985594     Document Type: Article
Times cited : (33)

References (103)
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    • Ojima, I.1    McCarthy, J.R.2    Welch, J.T.3
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    • Carbon-Fluorine Compounds Chemistry, Biochemistry and Biological Activities
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    • General Procedure for the Strecker Reaction of Aldehydes and Ketones Aldehyde or ketone (2 mmol)/fluorinated ketone (3 mmol, amine (2 mmol, TMSCN (3 mmol, and TMSOTf (5 mol, were taken in CH2Cl 2 (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 H2O and then extracted with CH2Cl2 (3 x 15 mL, All the organic layers were collected, washed with brine solution, and dried over anhyd Na 2SO4. 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 compa
    • 4. 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).


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