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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
journal contribution
posted on 2023-05-17, 19:21 authored by Ziegler, DT, Choi, J, Munoz-Molina, JM, Alexander BissemberAlexander Bissember, Peters, JC, Fu, GCThe 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.
History
Publication title
Journal of the American Chemical SocietyVolume
135Issue
35Pagination
13107-13112ISSN
0002-7863Department/School
School of Natural SciencesPublisher
American Chemical SocietyPlace of publication
1155 16Th St, Nw, Washington, USA, Dc, 20036Rights statement
Copyright 2013 American Chemical SocietyRepository Status
- Restricted