Catalytic alpha-arylation of imines leading to N-unprotected indoles and azaindoles
- Author
- Enrico Marelli, Martin Corpet, Yury Minenkov, Rifahath M Neyyappadath, Alessandro Bismuto, Giulia Buccolini, Massimiliano Curcio, Luigi Cavallo and Steven Nolan (UGent)
- 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
Citation
Please use this url to cite or link to this publication: http://hdl.handle.net/1854/LU-8168166
- 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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