Desulfonylation of amides using tributyltin hydride, samarium diiodide or zinc/titanium tetrachloride. A comparison of methods

Article abstract of DOI:10.1016/S0040-4020(00)00025-9

Deprotection of N-sulfonylated amides can be achieved by reaction with Bu₃SnH, SmI₂ or TiCl₄/Zn. All three methods gave good yields (typically >60%) when using N-benzoyl or related amides while the corresponding N~acetyl derivatives proved to be inert to deprotection under the same reaction conditions. The mechanistic implications of this are discussed. (C) 2000 Elsevier Science Ltd.