A Two-Coordinate Nickel Imido Complex That Effects C-H Amination

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This article discusses a two-coordinate nickel imido complex that effects C-H amination.

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3 p.

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Laskowski, Carl A.; Miller, Alexander J.M.; Hillhouse, Gregory L. & Cundari, Thomas R., 1964- December 22, 2010.

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This article discusses a two-coordinate nickel imido complex that effects C-H amination.

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3 p.

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Reprinted with permission from the Journal of the American Chemical Society. Copyright 2010 American Chemical Society.

Abstract: An exceptionally low coordinate nickel imido complex, (IPr*)Ni=N(dmp) (2) (dmp=2,6-dimesitylphenyl), has been prepared by the elimination of N₂ from a bulky aryl azide in its reaction with (IPr*)Ni(ɳ⁶-C₇H₈) (1). The solid-state structure of 2 features two-coordinate nickel with a linear C-Ni-N core and a short Ni-N distance, both indicative of multiple-bond character. Computational studies using density functional theory showed a Ni=N bond dominated by Ni(dπ)-N(pπ) interactions, resulting in two nearly degenerate singly occupied molecular orbitals (SOMOs) that are Ni-N π* in character. Reaction of 2 with CO resulted in nitrene-group transfer to form (dmp)NCO and (IPr*)Ni(CO)₃ (3). Net C-H insertion was observed in the reaction of 2 with ethene, forming the vinylamine (dmp)NH(CH=CH₂) (5) via an azanickelacyclobutane intermediate, (IPr*)Ni{N,C:k²-N(dmp)CH₂CH₂} (4).

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  • Journal of the American Chemical Society, 2010, Washington DC: American Chemical Society, pp. 771-773

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  • Publication Title: Journal of the American Chemical Society
  • Volume: 133
  • Issue: 4
  • Page Start: 771
  • Page End: 773
  • Peer Reviewed: Yes

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UNT Scholarly Works

The Scholarly Works Collection is home to materials from the University of North Texas community's research, creative, and scholarly activities and serves as UNT's Open Access Repository. It brings together articles, papers, artwork, music, research data, reports, presentations, and other scholarly and creative products representing the expertise in our university community.** Access to some items in this collection may be restricted.**

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  • December 22, 2010

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  • Oct. 9, 2012, 10:02 a.m.

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  • April 1, 2014, 12:43 p.m.

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Laskowski, Carl A.; Miller, Alexander J.M.; Hillhouse, Gregory L. & Cundari, Thomas R., 1964-. A Two-Coordinate Nickel Imido Complex That Effects C-H Amination, article, December 22, 2010; [Washington, D.C.]. (digital.library.unt.edu/ark:/67531/metadc107785/: accessed March 28, 2017), University of North Texas Libraries, Digital Library, digital.library.unt.edu; crediting UNT College of Arts and Sciences.