C-H Functionalization Reactivity of a Nickel-Imide

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This article discusses C-H functionalization reactivity of a Nickel-Imide.

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8 p.

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Wiese, Stefan; McAfee, Jason L.; Pahls, Dale R.; McMullin, Claire L.; Cundari, Thomas R., 1964- & Warren, Timothy H. May 22, 2012.

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This article discusses C-H functionalization reactivity of a Nickel-Imide.

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8 p.

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Reprinted with permission from the Journal of the American Chemical Society. Copyright 2012 American Chemical Society.

Abstract: We report report bifunctional reactivity of the β-diketiminato Ni(III)-imide [Me₃NN]Ni=NAd (1), which undergoes H-atom abstraction (HAA) reactions with benzylic substrates R-H (indane, ethylbenzene, toluene). Nickel-imide 1 competes with the nickel-amide HAA product [Me₃NN]Ni-NHAd (2) for the resulting hydrocarbyl radical R• to give the nickel-amide [Me₃NN]Ni-N(CHMePh)Ad (3) (R-H = ethylbenzene) or aminoalkyl tautomer [Me₃NN]Ni(ɳ²-CH(Ph)NHAd) (4) (R-H = toluene). A significant amount of functionalized amine R-NHAd is observed in the reaction of 1 with indane along with the dinickel imide {[Me₃NN]Ni}₂(μ-NAd) (5). Kinetic and DFT analyses point to rate-limiting HAA from R-H by 1 to give R•, which may add to either imide 1 or amide 2, each featuring significant N-based radical character. Thus, these studies illustrate a fundamental competition possible in C-H amination systems that proceed via a HAA/radical rebound mechanism.

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  • Journal of the American Chemical Society, 2012, Washington D.C.: American Chemical Society, pp. 10114-10121

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  • Publication Title: Journal of the American Chemical Society
  • Volume: 134
  • Issue: 24
  • Page Start: 10114
  • Page End: 10121
  • Peer Reviewed: Yes

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  • May 22, 2012

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  • Oct. 9, 2012, 10:02 a.m.

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  • Jan. 9, 2015, 5:09 p.m.

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Wiese, Stefan; McAfee, Jason L.; Pahls, Dale R.; McMullin, Claire L.; Cundari, Thomas R., 1964- & Warren, Timothy H. C-H Functionalization Reactivity of a Nickel-Imide, article, May 22, 2012; [Washington, D.C.]. (digital.library.unt.edu/ark:/67531/metadc107790/: accessed November 20, 2017), University of North Texas Libraries, Digital Library, digital.library.unt.edu; crediting UNT College of Arts and Sciences.