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Copper−Diamine-Catalyzed N-Arylation of Pyrroles, Pyrazoles, Indazoles, Imidazoles, and Triazoles

Jon C. Antilla, Jeremy M. Baskin, Timothy E. Barder, and Stephen L. Buchwald*

Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139

J. Org. Chem., 2004, 69 (17), pp 5578–5587

DOI: 10.1021/jo049658b

Publication Date (Web): July 10, 2004

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, sbuchwal@mit.edu

Abstract

This paper details the copper-catalyzed N-arylation of π-excessive nitrogen heterocycles. The coupling of either aryl iodides or aryl bromides with common nitrogen heterocycles (pyrroles, pyrazoles, indazoles, imidazoles, and triazoles) was successfully performed in good yield with catalysts derived from diamine ligands and CuI. General conditions were found that tolerate functional groups such as aldehydes, ketones, alcohols, primary amines, and nitriles on the aryl halide or heterocycle. Hindered aryl halides or heterocycles were also found to be suitable substrates using the conditions reported herein.

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Published In Issue August 20, 2004
Received March 1, 2004

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Article

Copper−Diamine-Catalyzed N-Arylation of Pyrroles, Pyrazoles, Indazoles, Imidazoles, and Triazoles

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A General and Efficient Copper Catalyst for the Amidation of Aryl Halides and the N-Arylation of Nitrogen Heterocycles

The Copper-Catalyzed N-Arylation of Indoles

A General and Efficient Copper Catalyst for the Amidation of Aryl Halides

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