Organic Chemistry Portal



Mild Deprotection of Primary N-(p-Toluenesulfonyl) Amides with SmI2 ­Following Trifluoroacetylation

Ziad Moussa, Daniel Romo*

*Department of Chemistry, Texas A&M University, P. O. Box 30012, College Station, TX 77842-3012, USA, Email:

Z. Moussa, D. Romo, Synlett, 2006, 3294-3298.

DOI: 10.1055/s-2006-951530


A mild deprotection for notoriously difficult to unmask primary N-(p-toluenesulfonyl) amides occurs at low temperature by initial activation of the nitrogen with a trifluoroacetyl group, followed by reductive cleavage of the p-toluenesulfonyl group with samarium diiodide.

see article for more examples

Key Words

toluenesulfonamides, samarium diiodide, reductive cleavage, trifluoroacetylation

ID: J60-Y2006-4800