Revisiting Iodine-mediated N-tert-Butoxycarbonylation of Amines
Ponugubati R. K. Murthia, Gondrala P. Kumar, Dandela Rambabua, Mandava V. B. Rao and Manojit Pal
Affiliation: Dr. Reddy's Institute of Life Sciences, University of Hyderabad Campus, Hyderabad-500 046, India.
Keywords: Amine, Catalysis, Iodine, Protecting group.
Revisiting the iodine mediated N-Boc (N-tert-butoxycarbonyl) protection of amines revealed that the reaction
can be performed using a lower quantity of iodine as a catalyst within a shorter reaction time. In addition to various aliphatic
and aromatic amines the reaction was found to be equally effective and selective for the N-Boc protection of amino
acid, guanidine, thiourea and N-(diaminomethylene)-1,1,1-trifluoromethanesulfonamide. The operational simplicity, high
yield, mild and solvent free nature are the other features of this process. In addition to reassessing the reported reaction
conditions and duration our study also demonstrates the further generality and versatility of this process.
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