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: romomail.chem.tamu.edu

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

DOI: 10.1055/s-2006-951530

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Abstract

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.

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Key Words

toluenesulfonamides, samarium diiodide, reductive cleavage, trifluoroacetylation

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ID: J60-Y2006-4800