Carbon-nitrogen bond formation involving well-defined aryl-copper(III) complexes

Lauren M Huffman; Shannon S Stahl

doi:10.1021/ja802123p

Carbon-nitrogen bond formation involving well-defined aryl-copper(III) complexes

J Am Chem Soc. 2008 Jul 23;130(29):9196-7. doi: 10.1021/ja802123p. Epub 2008 Jun 27.

Authors

Lauren M Huffman¹, Shannon S Stahl

Affiliation

¹ Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706, USA.

PMID: 18582057
DOI: 10.1021/ja802123p

Abstract

Carbon-heteroatom bond formation from copper(III) is commonly invoked as a key step in catalytic reactions, including the century-old Ullmann reactions. Well-defined examples of such reactions have never been observed. Here, we demonstrate that a well-defined Cu(III)-aryl species reacts with a variety nitrogen nucleophiles to undergo facile carbon-nitrogen bond formation.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Amides / chemistry
Amines / chemical synthesis*
Amines / chemistry
Copper / chemistry*
Hydrocarbons, Aromatic / chemistry*
Kinetics
Magnetic Resonance Spectroscopy / methods
Organometallic Compounds / chemistry*
Phthalimides / chemical synthesis
Phthalimides / chemistry
Pyridones / chemical synthesis
Pyridones / chemistry

Substances

Amides
Amines
Hydrocarbons, Aromatic
Organometallic Compounds
Phthalimides
Pyridones
Copper