Journal
DALTON TRANSACTIONS
Volume 50, Issue 36, Pages 12681-12691Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1dt02626g
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Funding
- US Department of Energy, Office of Basic Energy Sciences, Division of Materials Sciences and Engineering [DE-SC0020008]
- NSF [CHE-0650456, CHE0821346]
- NIH [S10 OD021758-01A1]
- U.S. Department of Energy (DOE) [DE-SC0020008] Funding Source: U.S. Department of Energy (DOE)
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Combining strain-promoted azide-alkyne cycloaddition (SPAAC) and inorganic click (iClick) reactivity allows access to metal 1,2,3-triazolates. Experimental and computational insights reveal that the iClick reactivity of metal azides depends on the accessibility of the azide functionality rather than electronic effects. Sterically unencumbered azide functionalities exhibit SPAAC iClick reactivity with cyclooctyne.
Combining strain-promoted azide-alkyne cycloaddition (SPAAC) and inorganic click (iClick) reactivity provides access to metal 1,2,3-triazolates. Experimental and computational insights demonstrate that iClick reactivity of the tested metal azides (LM-N-3, M = Au, W, Re, Ru and Pt) depends on the accessibility of the azide functionality rather than electronic effects imparted by the metal. SPAAC iClick reactivity with cyclooctyne is observed when the azide functionality is sterically unencumbered, e.g. [Au(N-3)(PPh3)] (Au-N-3), [W(eta(3)-allyl)(N-3)(bpy)(CO)(2)] (W-N-3), and [Re(N-3)(bpy)(CO)(3)] [bpy = 2,2'-bipyridine] (Re-N-3). Increased steric bulk and/or preequilibria with high activation barriers prevent SPAAC iClick reactivity for the complexes [Ru(N-3)(Tp)(PPh3)(2)] [Tp = tris(pyrazolyl)borate] (Ru-N-3), [Pt(N-3)(CH3)((PPr3)-Pr-i)(2)] [Pr-i = isopropyl] (Pt(II)-N-3), and [Pt(N-3)(CH3)(3)](4) ((PtN3)(4)). Based on these computational insights, the SPAAC iClick reactivity of [Pt(N-3)(CH3)(3)(P(CH3)(3))(2)] (Pt(IV)-N-3) was successfully predicted.
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