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Search for "ambiphilic reactivity" in Full Text gives 1 result(s) in Beilstein Journal of Organic Chemistry.

Metal–ligand multiple bonds as frustrated Lewis pairs for C–H functionalization

Matthew T. Whited

Beilstein J. Org. Chem. 2012, 8, 1554–1563, doi:10.3762/bjoc.8.177

demonstrate that the resultant reactivity may be a powerful tool for the functionalization of C–H and E–H bonds. Keywords: ambiphilic reactivity; C–H activation; C–H functionalization; frustrated Lewis pair; metal carbene; multiple bond; Introduction Orbital cooperation has long been recognized as an

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Scheme 1: Heterolytic cleavage of H₂ by a phosphine/borane FLP by H₂ polarization in the P–B cavity [5,11].

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Scheme 2: Insertion of carbon dioxide into a phosphine/borane FLP [14].

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Figure 1: Simplified frontier-molecular-orbital diagrams for (a) M^δ+═E^δ− and (b) M^δ−═E^δ+ FLPs (n = 1 for line...

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Figure 2: Quenching of M═E FLPs by dimerization: (a) generic M^δ+═E^δ− case, and (b) Bergman's arylimido zircon...

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Scheme 3: Oxygen-atom extrusion from CO₂ by a Ta(V) neopentylidene [27].

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Scheme 4: Oxygen-atom transfer from acetone at a Zr(IV) imide [28].

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Scheme 5: Alkyne cycloaddition at a Zr(IV) imide [38].

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Scheme 6: Nitrile-alkyne cross metathesis at a W(VI) nitride [40,41].

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Scheme 7: C–H and H–H addition across a zirconium(IV) imide [42].

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Scheme 8: Formal [2 + 2] cycloaddition of methyl isocyanate at a ruthenium silylene [58].

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Scheme 9: Oxygen-atom transfer from phenyl isocyanate to a cationic terminal borylene [60].

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Scheme 10: Coupling of a phosphorus ylide with an iridium methylene [62].

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Scheme 11: Reactions of (PNP)Ir═C(H)Ot-Bu with oxygen-containing heterocumulenes [71].

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Scheme 12: Reductive coupling of two CS₂ units at (PNP)Ir═C(H)Ot-Bu [73].

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Figure 3: Single-crystal X-ray structure of a silver(I) triflate adduct of (PNP)Ir═C(H)Ot-Bu with most H atom...

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Scheme 13: Possible routes to C–H functionalization by 1,2-addition across a polarized metal–element multiple ...

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Scheme 14: Alkoxycarbene formation by double C–H activation at (PNP)Ir [88].

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Scheme 15: Catalytic oxidation of MTBE by multiple C–H activations and nitrene-group transfer to a M^δ−═E^δ+ FLP ...

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Published 18 Sep 2012

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