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

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journal contribution
posted on 15.10.2010, 00:00 by Jeffrey S. Arnold, Robert F. Stone, Hien M. Nguyen
The use of unactivated aromatic amines in the rhodium-catalyzed regioselective amination of secondary allylic trichloroacetimidates is explored. The desired N-arylamines are obtained 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. Control studies show that rhodium is not simply acting as a Lewis acid to activate the trichloroacetimidate leaving group.