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Article

Synthesis of Medium Ring Nitrogen Heterocycles via a Tandem Copper-Catalyzed C−N Bond Formation−Ring-Expansion Process

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Artis Klapars, Sean Parris, Kevin W. Anderson, and Stephen L. Buchwald*

Contribution from the Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139

J. Am. Chem. Soc., 2004, 126 (11), pp 3529–3533

DOI: 10.1021/ja038565t

Publication Date (Web): March 2, 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

A simple method for the preparation of medium ring heterocycles (7-, 8-, 9-, and 10-membered) has been developed. The process employs a Cu-catalyzed coupling of a β-lactam with an aryl bromide or iodide followed by intramolecular attack of a pendant amino group. In some instances, the intermediate β-lactam is observable but can be converted to the aza-heterocycle by catalysis. Acetic acid was found to be superior to transition metal complexes as a catalyst for this ring-expansion process.

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Published In Issue March 24, 2004
Received September 17, 2003

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Article

Synthesis of Medium Ring Nitrogen Heterocycles via a Tandem Copper-Catalyzed C−N Bond Formation−Ring-Expansion Process

Abstract

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Recommend & Share

Related Content

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

Highly Selective Room-Temperature Copper-Catalyzed C−N Coupling Reactions Highly Selective Room-Temperature Copper-Catalyzed C−N Coupling Reactions

The Copper-Catalyzed N-Arylation of Indoles

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