Synthesis of α,α-Disubstituted Aryl Amines by Rhodium-Catalyzed Amination of Tertiary Allylic Trichloroacetimidates

Jeffrey S. Arnold, Gregory T. Cizio and Hien M. Nguyen*

*Department of Chemistry, University of Iowa, Iowa City, Iowa 52242, United States, Email: hien-nguyenuiowa.edu

J. S. Arnold, G. T. Cizio, H. M. Nguyen, Org. Lett., 2011, 13, 5576-5579.

DOI: 10.1021/ol202313y

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Abstract

A rhodium-catalyzed regioselective amination of tertiary allylic trichloroacetimidates with unactivated aromatic amines is a direct and efficient approach to the preparation of α,α-disubstituted allylic aryl amines in good yield and with excellent regioselectivity. This method enables the conversion of unactivated primary and secondary amines and the preparation of reverse prenylated indoles in two steps.

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Rhodium-Catalyzed Dynamic Kinetic Asymmetric Transformations of Racemic Tertiary Allylic Trichloroacetimidates with Anilines

J. S. Arnold, H. M. Nguyen, J. Am. Chem. Soc., 2012, 134, 8380-8383.

Rhodium-Catalyzed Regioselective Amination of Secondary Allylic Trichloroacetimidates with Unactivated Aromatic Amines

J. S. Arnold, R. F. Stone, H. M. Nguyen, Org. Lett., 2010, 12, 4580-4583.

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Key Words

Allylic Amines, Aryl Amines

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ID: J54-Y2011-3080