Bissember, Alex C. and Lundgren, Rylan J. and Creutz, Sidney E. and Peters, Jonas C. and Fu, Gregory C. (2013) Transition-Metal-Catalyzed Alkylations of Amines with Alkyl Halides: Photoinduced, Copper-Catalyzed Couplings of Carbazoles. Angewandte Chemie International Edition, 52 (19). pp. 5129-5133. ISSN 1433-7851. doi:10.1002/anie.201301202. https://resolver.caltech.edu/CaltechAUTHORS:20130620-145951306
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Abstract
N-alkylations of carbazoles with a variety of secondary and hindered primary alkyl iodides can be achieved by using a simple precatalyst (CuI) under mild conditions (0 °C) in the presence of a Brønsted base; at higher temperature (30 °C), secondary alkyl bromides also serve as suitable coupling partners. A Li[Cu(carbazolide)_2] complex has been crystallographically characterized, and it may serve as an intermediate in the catalytic cycle.
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| Additional Information: | © 2013 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. Received: February 11, 2013; Published online: April 8, 2013. This work was supported by the Gordon and Betty Moore Foundation (grant to J.C.P.), the National Science Foundation (fellowship support for S.E.C.), and the Natural Sciences and Engineering Research Council of Canada (fellowship support for R.J.L.). Assistance with X-ray crystallography from Larry M. Henling is gratefully acknowledged. | |||||||||
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| Subject Keywords: | alkylations; amine; copper; homogeneous catalysis; photochemistry | |||||||||
| Issue or Number: | 19 | |||||||||
| DOI: | 10.1002/anie.201301202 | |||||||||
| Record Number: | CaltechAUTHORS:20130620-145951306 | |||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20130620-145951306 | |||||||||
| Official Citation: | Bissember, A. C., Lundgren, R. J., Creutz, S. E., Peters, J. C. and Fu, G. C. (2013), Transition-Metal-Catalyzed Alkylations of Amines with Alkyl Halides: Photoinduced, Copper-Catalyzed Couplings of Carbazoles . Angew. Chem. Int. Ed., 52: 5129–5133. doi: 10.1002/anie.201301202 | |||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | |||||||||
| ID Code: | 39006 | |||||||||
| Collection: | CaltechAUTHORS | |||||||||
| Deposited By: | Tony Diaz | |||||||||
| Deposited On: | 21 Jun 2013 18:26 | |||||||||
| Last Modified: | 09 Nov 2021 23:41 |
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