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 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
UTAS Author:	Bissember, AC (Dr Alex Bissember)
ID Code:	86303
Year Published:	2013
Web of Science® Times Cited:	108
Deposited By:	Chemistry
Deposited On:	2013-09-04
Last Modified:	2013-10-21
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