Design, synthesis, and carbon-heteroatom coupling reactions of organometallic nickel(IV) complexes

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Science  05 Feb 2015:
DOI: 10.1126/science.aaa4526

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Homogeneous nickel catalysis is employed for the synthesis of pharmaceuticals, natural products, and polymers. These reactions generally proceed via nickel intermediates in the Ni0, NiI, NiII, and/or NiIII oxidation states. In contrast, NiIV intermediates are rarely accessible. We report herein the design, synthesis, and characterization of a series of organometallic NiIV complexes, accessed by the reaction of NiII precursors with the widely used oxidant, (S-(trifluoromethyl)dibenzothiophenium)triflate. These NiIV complexes undergo highly selective carbon(sp3)-oxygen, carbon(sp3)-nitrogen, and carbon(sp3)-sulfur coupling reactions with exogenous nucleophiles. The observed reactivity has the potential for direct applications in the development of nickel-catalyzed carbon-heteroatom coupling reactions.

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