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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

DOI: doi:10.1021/ja4060806

Abstract

The use of light to facilitate copper-catalyzed cross-couplings of nitrogen nucleophiles can enable CN 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 CN 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
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
Author:Bissember, AC (Dr Alex Bissember)
ID Code:86303
Year Published:2013
Web of Science® Times Cited:75
Deposited By:Chemistry
Deposited On:2013-09-04
Last Modified:2013-10-21
Downloads:0

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