Volume 32, Issue 18
Isocyclic Compounds
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ChemInform Abstract: The Copper-Mediated Cross-Coupling of Phenylboronic Acids and N-Hydroxyphthalimide at Room Temperature: Synthesis of Aryloxyamines.

H. Michael Petrassi

H. Michael Petrassi

Dep. Chem., Scripps Res. Inst., San Diego, La Jolla, CA 92037, USA

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K. Barry Sharpless

K. Barry Sharpless

Dep. Chem., Scripps Res. Inst., San Diego, La Jolla, CA 92037, USA

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Jeffery W. Kelly

Jeffery W. Kelly

Dep. Chem., Scripps Res. Inst., San Diego, La Jolla, CA 92037, USA

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First published: 27 May 2010

Abstract

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ChemInform Abstract

A novel synthetic access to aryloxyamines (III) and (VI) is presented, involving the copper-mediated coupling of arylboronic acids (II) and (V) with N-hydroxyphthalimide (I) in the presence of base. A wide range of electron-donating or electron-withdrawing substituents at the aryl group is tolerated. Removal of the phthalimide group is simply achieved with hydrazine.

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