A five-coordinate nickel(II) fluoroalkyl complex as a precursor to a spectroscopically detectable Ni(III) species
Mechanistic proposals for nickel-catalyzed coupling reactions often invoke five-coordinate alkyl- or aryl-bound Ni(II) and/or high-valent nickel(III) species, but because of their reactive nature, they have been difficult to study and fingerprint. In this work, we invoked the stabilizing properties...
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| Published in: | Journal of the American Chemical Society Vol. 135; no. 22; p. 8141 |
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| Main Authors: | , , , , , , , , |
| Format: | Journal Article |
| Language: | English |
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United States
05.06.2013
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| ISSN: | 1520-5126, 1520-5126 |
| Online Access: | Get more information |
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| Abstract | Mechanistic proposals for nickel-catalyzed coupling reactions often invoke five-coordinate alkyl- or aryl-bound Ni(II) and/or high-valent nickel(III) species, but because of their reactive nature, they have been difficult to study and fingerprint. In this work, we invoked the stabilizing properties of fluoroalkyl ligands to access such nickel species bearing ligands that are commonplace in organic coupling reactions. We show that five-coordinate Ni(II) complexes containing nickel-carbon bonds can readily be prepared given the appropriate precursor, and we also present evidence for the formation of Ni(III) species upon chemical and electrochemical oxidation of the five-coordinate complexes. |
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| AbstractList | Mechanistic proposals for nickel-catalyzed coupling reactions often invoke five-coordinate alkyl- or aryl-bound Ni(II) and/or high-valent nickel(III) species, but because of their reactive nature, they have been difficult to study and fingerprint. In this work, we invoked the stabilizing properties of fluoroalkyl ligands to access such nickel species bearing ligands that are commonplace in organic coupling reactions. We show that five-coordinate Ni(II) complexes containing nickel-carbon bonds can readily be prepared given the appropriate precursor, and we also present evidence for the formation of Ni(III) species upon chemical and electrochemical oxidation of the five-coordinate complexes. Mechanistic proposals for nickel-catalyzed coupling reactions often invoke five-coordinate alkyl- or aryl-bound Ni(II) and/or high-valent nickel(III) species, but because of their reactive nature, they have been difficult to study and fingerprint. In this work, we invoked the stabilizing properties of fluoroalkyl ligands to access such nickel species bearing ligands that are commonplace in organic coupling reactions. We show that five-coordinate Ni(II) complexes containing nickel-carbon bonds can readily be prepared given the appropriate precursor, and we also present evidence for the formation of Ni(III) species upon chemical and electrochemical oxidation of the five-coordinate complexes.Mechanistic proposals for nickel-catalyzed coupling reactions often invoke five-coordinate alkyl- or aryl-bound Ni(II) and/or high-valent nickel(III) species, but because of their reactive nature, they have been difficult to study and fingerprint. In this work, we invoked the stabilizing properties of fluoroalkyl ligands to access such nickel species bearing ligands that are commonplace in organic coupling reactions. We show that five-coordinate Ni(II) complexes containing nickel-carbon bonds can readily be prepared given the appropriate precursor, and we also present evidence for the formation of Ni(III) species upon chemical and electrochemical oxidation of the five-coordinate complexes. |
| Author | Wang, Huan Xu, Long Stirnat, Kathrin Klein, Axel Biewer, Christian Vicic, David A Gomez-Benitez, Valente Yamaguchi, Yoshitaka Zhang, Cheng-Pan |
| Author_xml | – sequence: 1 givenname: Cheng-Pan surname: Zhang fullname: Zhang, Cheng-Pan organization: Department of Chemistry, University of Hawaii , 2545 McCarthy Mall, Honolulu, Hawaii 96822, United States – sequence: 2 givenname: Huan surname: Wang fullname: Wang, Huan – sequence: 3 givenname: Axel surname: Klein fullname: Klein, Axel – sequence: 4 givenname: Christian surname: Biewer fullname: Biewer, Christian – sequence: 5 givenname: Kathrin surname: Stirnat fullname: Stirnat, Kathrin – sequence: 6 givenname: Yoshitaka surname: Yamaguchi fullname: Yamaguchi, Yoshitaka – sequence: 7 givenname: Long surname: Xu fullname: Xu, Long – sequence: 8 givenname: Valente surname: Gomez-Benitez fullname: Gomez-Benitez, Valente – sequence: 9 givenname: David A surname: Vicic fullname: Vicic, David A |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/23692548$$D View this record in MEDLINE/PubMed |
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