Reactive dications: the superacid-catalyzed reactions of alkynes bearing adjacent N-heterocycles or amine groups.
A variety of aminoalkynes and related heterocycles are reacted in the Bronsted superacid CF(3)SO(3)H (triflic acid), and products are obtained in generally good yields (69-99%) from Friedel-Crafts-type reactions. The reactions are consistent with the formation of novel dicationic intermediates having a vinyl cationic site and an adjacent protonated N-heterocycle or ammonium cation.
Klumpp
Douglas A
DA
Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, Illinois 60115, USA. dklumpp@niu.edu
Rendy
Rendy
R
Zhang
Yun
Y
McElrea
Aaron
A
Gomez
Alma
A
Dang
Han
H
D000480:Alkynes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D002412:Cations / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000737:chemistry*; D007202:Indicators and Reagents; D015394:Molecular Structure; D000644:Quaternary Ammonium Compounds / Q000737:chemistry
D000480:Alkynes; D000588:Amines; D002412:Cations; D006571:Heterocyclic Compounds; D007202:Indicators and Reagents; D000644:Quaternary Ammonium Compounds