Synthesis of N-Aryl Hydrazides by Copper-Catalyzed Coupling of Hydrazides with Aryl Iodides

Martina Wolter, Artis Klapars and Stephen L. Buchwald

*Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, Email: sbuchwalmit.edu

M. Wolter, A. Klapars, S. L. Buchwald, Org. Lett., 2001, 3, 3803-3805.

DOI: 10.1021/ol0168216

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Abstract

CuI catalyzes a convenient intermolecular N-arylation of hydrazides with para- and meta-substituted aryl iodides in the presence Cs₂CO₃. A reversal in regioselectivity is observed for the arylation of benzoic hydrazide with ortho-substituted aryl iodides.

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Copper-Catalyzed Coupling of Alkylamines and Aryl Iodides: An Efficient System Even in an Air Atmosphere

F. Y. Kwong, A. Klapars, S. L. Buchwald, Org. Lett., 2002, 4, 581-584.

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Key Words

Ullmann Reaction, Hydrazides

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ID: J54-Y2001