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Accueil > Publications > Recherche par années > Années 2000 > 2007

Aucagne, V ; Berna, J ; Crowley, JD ; Goldup, SM ; Haenni, KD ; Leigh, DA ; Lusby, PJ ; Ronaldson, VE ; Slawin, AMZ ; Viterisi, A ; Walker, DB

Catalytic "Active-Metal" template synthesis of [2]rotaxanes, [3]rotaxanes, and molecular shuttles, and some observations on the mechanism of the Cu(I)-catalyzed azide-alkyne 1,3-cycloaddition

Journal of The American Chemical Society 129 11950-11963

par Administrateur - publié le

Abstract :

A synthetic approach to rotaxane architectures is described in which metal atoms catalyze covalent bond formation while simultaneously acting as the template for the assembly of the mechanically interlocked structure. This "active- metal" template strategy is exemplified using the Huisgen-Meldal-Fokin Cu(l)catalyzed 1,3-cycloaddition of azides with terminal alkynes (the CuAAC "click" reaction). Coordination of Cu(I) to an endotopic pyridine-containing macrocycle allows the alkyne and azide to bind to metal atoms in such a way that the metal-mediated bond-forming reaction takes place through the cavity of the macrocycle-or macrocycles-forming a rotaxane.