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Catalytic alpha-arylation of imines leading to N-unprotected indoles and azaindoles

(2016) ACS CATALYSIS. 6(5). p.2930-2938
Author
Organization
Abstract
A palladium N-heterocyclic carbene catalyzed methodology for the synthesis of substituted, N-unprotected indoles and azaindoles is reported. The protocol permits access to various, highly substituted members of these classes of compounds. Although two possible reaction pathways (deprotonative and Heck-like) can be proposed, control experiments, supported by computational studies, point toward a deprotonative mechanism being operative.
Keywords
cross-coupling, NHC, indole, heterocyclic compounds, ketone arylation, ligand effect, CROSS-COUPLING REACTIONS, ONE-POT SYNTHESIS, HIGHLY SUBSTITUTED INDOLES, ARYL HALIDES, ENOLATE ARYLATION, SUZUKI-MIYAURA, C-N, CARBENE COMPLEXES, MODULAR SYNTHESIS, BOND FORMATION

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MLA
Marelli, Enrico, et al. “Catalytic Alpha-Arylation of Imines Leading to N-Unprotected Indoles and Azaindoles.” ACS CATALYSIS, vol. 6, no. 5, 2016, pp. 2930–38.
APA
Marelli, E., Corpet, M., Minenkov, Y., Neyyappadath, R. M., Bismuto, A., Buccolini, G., … Nolan, S. (2016). Catalytic alpha-arylation of imines leading to N-unprotected indoles and azaindoles. ACS CATALYSIS, 6(5), 2930–2938.
Chicago author-date
Marelli, Enrico, Martin Corpet, Yury Minenkov, Rifahath M Neyyappadath, Alessandro Bismuto, Giulia Buccolini, Massimiliano Curcio, Luigi Cavallo, and Steven Nolan. 2016. “Catalytic Alpha-Arylation of Imines Leading to N-Unprotected Indoles and Azaindoles.” ACS CATALYSIS 6 (5): 2930–38.
Chicago author-date (all authors)
Marelli, Enrico, Martin Corpet, Yury Minenkov, Rifahath M Neyyappadath, Alessandro Bismuto, Giulia Buccolini, Massimiliano Curcio, Luigi Cavallo, and Steven Nolan. 2016. “Catalytic Alpha-Arylation of Imines Leading to N-Unprotected Indoles and Azaindoles.” ACS CATALYSIS 6 (5): 2930–2938.
Vancouver
1.
Marelli E, Corpet M, Minenkov Y, Neyyappadath RM, Bismuto A, Buccolini G, et al. Catalytic alpha-arylation of imines leading to N-unprotected indoles and azaindoles. ACS CATALYSIS. 2016;6(5):2930–8.
IEEE
[1]
E. Marelli et al., “Catalytic alpha-arylation of imines leading to N-unprotected indoles and azaindoles,” ACS CATALYSIS, vol. 6, no. 5, pp. 2930–2938, 2016.
@article{8168166,
  abstract     = {A palladium N-heterocyclic carbene catalyzed methodology for the synthesis of substituted, N-unprotected indoles and azaindoles is reported. The protocol permits access to various, highly substituted members of these classes of compounds. Although two possible reaction pathways (deprotonative and Heck-like) can be proposed, control experiments, supported by computational studies, point toward a deprotonative mechanism being operative.},
  author       = {Marelli, Enrico and Corpet, Martin and Minenkov, Yury and Neyyappadath, Rifahath M and Bismuto, Alessandro and Buccolini, Giulia and Curcio, Massimiliano and Cavallo, Luigi and Nolan, Steven},
  issn         = {2155-5435},
  journal      = {ACS CATALYSIS},
  keywords     = {cross-coupling,NHC,indole,heterocyclic compounds,ketone arylation,ligand effect,CROSS-COUPLING REACTIONS,ONE-POT SYNTHESIS,HIGHLY SUBSTITUTED INDOLES,ARYL HALIDES,ENOLATE ARYLATION,SUZUKI-MIYAURA,C-N,CARBENE COMPLEXES,MODULAR SYNTHESIS,BOND FORMATION},
  language     = {eng},
  number       = {5},
  pages        = {2930--2938},
  title        = {Catalytic alpha-arylation of imines leading to N-unprotected indoles and azaindoles},
  url          = {http://dx.doi.org/10.1021/acscatal.6b00040},
  volume       = {6},
  year         = {2016},
}

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