Gallium (III) triflate catalyzed efficient Strecker reaction of ketones and their fluorinated analogs.
The synthesis of alpha-aminonitriles and their fluorinated analogs has been carried out in high yield and purity by the Strecker reaction from the corresponding ketones and amines with trimethylsilyl cyanide using gallium triflate in dichloromethane. Monofluoro-, difluro-, or trifluoromethyl groups can be incorporated into the alpha-aminonitrile product by varying the nature of the fluorinated ketones. Study with various fluorinated and nonfluorinated ketones reveals that the choice of proper catalyst and the solvent system (suitable metal triflates as a catalyst and dichloromethane as a solvent) plays the key role in the direct Strecker reactions of ketones.
Prakash
G K Surya
GK
Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, University Park, Los Angeles, CA 90089-1661.
Mathew
Thomas
T
Panja
Chiradeep
C
Alconcel
Steevens
S
Vaghoo
Habiba
H
Do
Clement
C
Olah
George A
GA
D000447:Aldehydes / Q000737:chemistry; D002384:Catalysis; D002621:Chemistry / Q000379:methods; D005461:Fluorine / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D008698:Mesylates / Q000737:chemistry*; D008752:Methylene Chloride / Q000737:chemistry; D008956:Models, Chemical; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry; D012997:Solvents
D000447:Aldehydes; D007659:Ketones; D008698:Mesylates; D009570:Nitriles; D012997:Solvents; C516572:gallium triflate; D005461:Fluorine; D008752:Methylene Chloride