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General and mild Ni-0-catalyzed alpha-arylation of ketones using aryl chlorides

(2015) CHEMISTRY-A EUROPEAN JOURNAL. 21(10). p.3906-3909
Author
Organization
Abstract
A general methodology for the alpha-arylation of ketones using a nickel catalyst has been developed. The new well-defined [Ni(IPr*)(cin) Cl] (1c) pre-catalyst showed great efficiency for this transformation, allowing the coupling of a wide range of ketones, including acetophenone derivatives, with various functionalised aryl chlorides. This cinnamyl-based Ni-N-heterocyclic carbene (NHC) complex has demonstrated a different behaviour to previously reported NHC-Ni catalysts. Preliminary mechanistic studies suggest a Ni-0/Ni-II catalytic cycle to be at play.
Keywords
aryl chlorides, cross-coupling reactions, ketone arylation, N-heterocyclic carbenes, nickel, synthetic methods, CATALYZED CARBOXYLATION, ACYCLIC KETONES, SUZUKI-MIYAURA, C-N, COMPLEXES, HALIDES, AMIDES, ACETONE, DERIVATIVES, SELECTIVITY

Citation

Please use this url to cite or link to this publication:

MLA
Fernandez-Salas, Jose A., et al. “General and Mild Ni-0-Catalyzed Alpha-Arylation of Ketones Using Aryl Chlorides.” CHEMISTRY-A EUROPEAN JOURNAL, vol. 21, no. 10, 2015, pp. 3906–09.
APA
Fernandez-Salas, J. A., Marelli, E., Cordes, D. B., Slawin, A. M., & Nolan, S. (2015). General and mild Ni-0-catalyzed alpha-arylation of ketones using aryl chlorides. CHEMISTRY-A EUROPEAN JOURNAL, 21(10), 3906–3909.
Chicago author-date
Fernandez-Salas, Jose A, Enrico Marelli, David B Cordes, Alexandra MZ Slawin, and Steven Nolan. 2015. “General and Mild Ni-0-Catalyzed Alpha-Arylation of Ketones Using Aryl Chlorides.” CHEMISTRY-A EUROPEAN JOURNAL 21 (10): 3906–9.
Chicago author-date (all authors)
Fernandez-Salas, Jose A, Enrico Marelli, David B Cordes, Alexandra MZ Slawin, and Steven Nolan. 2015. “General and Mild Ni-0-Catalyzed Alpha-Arylation of Ketones Using Aryl Chlorides.” CHEMISTRY-A EUROPEAN JOURNAL 21 (10): 3906–3909.
Vancouver
1.
Fernandez-Salas JA, Marelli E, Cordes DB, Slawin AM, Nolan S. General and mild Ni-0-catalyzed alpha-arylation of ketones using aryl chlorides. CHEMISTRY-A EUROPEAN JOURNAL. 2015;21(10):3906–9.
IEEE
[1]
J. A. Fernandez-Salas, E. Marelli, D. B. Cordes, A. M. Slawin, and S. Nolan, “General and mild Ni-0-catalyzed alpha-arylation of ketones using aryl chlorides,” CHEMISTRY-A EUROPEAN JOURNAL, vol. 21, no. 10, pp. 3906–3909, 2015.
@article{8168339,
  abstract     = {A general methodology for the alpha-arylation of ketones using a nickel catalyst has been developed. The new well-defined [Ni(IPr*)(cin) Cl] (1c) pre-catalyst showed great efficiency for this transformation, allowing the coupling of a wide range of ketones, including acetophenone derivatives, with various functionalised aryl chlorides. This cinnamyl-based Ni-N-heterocyclic carbene (NHC) complex has demonstrated a different behaviour to previously reported NHC-Ni catalysts. Preliminary mechanistic studies suggest a Ni-0/Ni-II catalytic cycle to be at play.},
  author       = {Fernandez-Salas, Jose A and Marelli, Enrico and Cordes, David B and Slawin, Alexandra MZ and Nolan, Steven},
  issn         = {0947-6539},
  journal      = {CHEMISTRY-A EUROPEAN JOURNAL},
  keywords     = {aryl chlorides,cross-coupling reactions,ketone arylation,N-heterocyclic carbenes,nickel,synthetic methods,CATALYZED CARBOXYLATION,ACYCLIC KETONES,SUZUKI-MIYAURA,C-N,COMPLEXES,HALIDES,AMIDES,ACETONE,DERIVATIVES,SELECTIVITY},
  language     = {eng},
  number       = {10},
  pages        = {3906--3909},
  title        = {General and mild Ni-0-catalyzed alpha-arylation of ketones using aryl chlorides},
  url          = {http://dx.doi.org/10.1002/chem.201406457},
  volume       = {21},
  year         = {2015},
}

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