Organic Chemistry Portal



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

Jeffrey S. Arnold, Robert F. Stone and Hien M. Nguyen*

*Department of Chemistry, University of Iowa, Iowa City, Iowa 52242, United States, Email:

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

DOI: 10.1021/ol1019025 (free Supporting Information)


A rhodium-catalyzed regioselective amination of secondary allylic trichloroacetimidates with unactivated aromatic amines gives N-arylamines in high yields and regioselectivity, favoring the branched amination products. The presence of the trichloroacetimidate leaving group was found to be critical for successful regioselective amination reactions with unactivated aromatic amines.

see article for more examples

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

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

Key Words

Allylic Amines, Aryl Amines

ID: J54-Y2010-2880