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JOURNAL ARTICLE
RESEARCH SUPPORT, N.I.H., EXTRAMURAL
RESEARCH SUPPORT, NON-U.S. GOV'T
RESEARCH SUPPORT, U.S. GOV'T, NON-P.H.S.
Dicopper Cu(I)Cu(I) and Cu(I)Cu(II) Complexes in Copper-Catalyzed Azide-Alkyne Cycloaddition.
Journal of the American Chemical Society 2017 April 20
A discrete, dicopper μ-alkynyl complex, [Cu2 (μ-η1 :η1 -C≡C(C6 H4 )CH3 )DPFN]NTf2 (DPFN = 2,7-bis(fluoro-di(2-pyridyl)methyl)-1,8-naphthyridine; NTf2 - = N(SO2 CF3 )2 - ), reacts with p-tolylazide to yield a dicopper complex with a symmetrically bridging 1,2,3-triazolide, [Cu2 (μ-η1 :η1 -(1,4-bis(4-tolyl)-1,2,3-triazolide))DPFN]NTf2 . This transformation exhibits bimolecular reaction kinetics and represents a key step in a proposed, bimetallic mechanism for copper-catalyzed azide-alkyne cycloaddition (CuAAC). The μ-alkynyl and μ-triazolide complexes undergo reversible redox events (by cyclic voltammetry), suggesting that a cycloaddition pathway involving mixed-valence dicopper species might also be possible. Synthesis and characterization of the mixed-valence μ-alkynyl dicopper complex, [Cu2 (μ-η1 :η1 -C≡C(C6 H4 )CH3 )DPFN](NTf2 )2 , revealed an electronic structure with an unexpected partially delocalized spin, as evidenced by electron paramagnetic resonance spectroscopy. Studies of the mixed-valence μ-alkynyl complex's reactivity suggest that a mixed-valence pathway is less likely than one involving intermediates with only copper(I).
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