Abstract
An ionic Cu(I) complex (Cu(I)@Qun-β-CD), stabilized by water soluble quinolinium modified β-cyclodextrin (Qun-β-CD) with an 8-N-pentyl side chain, was prepared and characterized by ESI-Mass, NMR and UV-Visible spectroscopies and also molecular modeling studies. The synthesized Cu(I)@Qun-β-CD was found to be highly efficient in promoting A3-coupling reaction of various aldehydes, amines and terminal alkynes to yield propargylamines in acetonitrile medium. The prepared Qun-β-CD (C) alone, without any metal ion, follows a different course exhibiting excellent catalytic efficiency in an intramolecular tandem cyclisation reaction of the same reagents to yield quinolines in aqueous medium. From the point of the environmental concerns, the work presented here has the merits of both three-component reaction, environmentally friendliness, easy separation, simple work-up, good yields, the avoidance of organic solvents and use of an inexpensive catalyst. The catalyst was recycled more than five consecutive cycles without any significant loss in its activity in both reactions.
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