A rate enhancement of tert-butoxycarbonylation of aromatic amines with Boc2O in alcoholic solvents |
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| Authors: | Tirayut Vilaivan |
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| Institution: | Organic Synthesis Research Unit, Department of Chemistry, Faculty of Science, Chulalongkorn University, Phayathai Road, Patumwan, Bangkok 10330, Thailand |
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| Abstract: | A rate enhancement of tert-butoxycarbonylation of aromatic amines by Boc2O in alcohols compared to aprotic solvents was demonstrated. Kinetic analysis by NMR suggested that the reaction in CD3OD was faster than in CDCl3 by a factor of 70. Reactions between Boc2O and various aliphatic and aromatic amines in ethanol provided the N-Boc derivatives in good to excellent yields in short reaction times. |
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| Keywords: | Amine Boc2O Protecting group |
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