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A versatile approach to Ullmann C-N couplings at room temperature: New families of nucleophiles and electrophiles for photoinduced, copper-catalyzed processes
Citation
Ziegler, DT and Choi, J and Munoz-Molina, JM and Bissember, AC and Peters, JC and Fu, GC, A versatile approach to Ullmann C-N couplings at room temperature: New families of nucleophiles and electrophiles for photoinduced, copper-catalyzed processes, Journal of the American Chemical Society, 135, (35) pp. 13107-13112. ISSN 0002-7863 (2013) [Refereed Article]
Copyright Statement
Copyright 2013 American Chemical Society
Abstract
The use of light to facilitate copper-catalyzed cross-couplings of nitrogen nucleophiles can enable C–N bond formation to occur under unusually mild conditions. In this study, we substantially expand the scope of such processes, establishing that this approach is not limited to reactions of carbazoles with iodobenzene and alkyl halides. Specifically, we demonstrate for the first time that other nitrogen nucleophiles (e.g., common pharmacophores such as indoles, benzimidazoles, and imidazoles) as well as other electrophiles (e.g., hindered/deactivated/heterocyclic aryl iodides, an aryl bromide, an activated aryl chloride, alkenyl halides, and an alkynyl bromide) serve as suitable partners. Photoinduced C–N bond formation can be achieved at room temperature using a common procedure with an inexpensive catalyst (CuI) that does not require a ligand coadditive and is tolerant of moisture and a variety of functional groups.
Item Details
Item Type: | Refereed Article |
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Research Division: | Chemical Sciences |
Research Group: | Organic chemistry |
Research Field: | Organic chemical synthesis |
Objective Division: | Expanding Knowledge |
Objective Group: | Expanding knowledge |
Objective Field: | Expanding knowledge in the chemical sciences |
UTAS Author: | Bissember, AC (Associate Professor Alex Bissember) |
ID Code: | 86303 |
Year Published: | 2013 |
Web of Science® Times Cited: | 149 |
Deposited By: | Chemistry |
Deposited On: | 2013-09-04 |
Last Modified: | 2013-10-21 |
Downloads: | 0 |
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