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Communication

The Role of Chelating Diamine Ligands in the Goldberg Reaction: A Kinetic Study on the Copper-Catalyzed Amidation of Aryl Iodides

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Eric R. Strieter,^† Donna G. Blackmond,^‡ and Stephen L. Buchwald*^†

Contribution from the Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, and the Department of Chemistry, Imperial College, London SW7 2AZ, U.K.

J. Am. Chem. Soc., 2005, 127 (12), pp 4120–4121

DOI: 10.1021/ja050120c

Publication Date (Web): February 26, 2005

†

Massachusetts Institute of Technology.

‡

Imperial College.

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

The mechanistic details of the Cu-catalyzed amidation of aryl iodides are presented. The kinetic data suggest that the diamine ligand prevents multiple ligation of the amide. The formation of an amidocuprate species external to the catalytic cycle helped to rationalize the dependence on diamine concentration and the inverse dependence on amide concentration at low diamine concentrations. The intermediacy of a Cu(I) amidate was established through both its chemical and kinetic competency.

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Published In Issue March 30, 2005
Received January 8, 2005

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Communication

The Role of Chelating Diamine Ligands in the Goldberg Reaction: A Kinetic Study on the Copper-Catalyzed Amidation of Aryl Iodides

Abstract

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SciFinder Links

History

Recommend & Share

Related Content

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

Expanding Pd-Catalyzed C−N Bond-Forming Processes: The First Amidation of Aryl Sulfonates, Aqueous Amination, and Complementarity with Cu-Catalyzed Reactions

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

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