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

Authors
Knowles, HS Parsons, AF Pettifer, RM Rickling, S
Citation
Hs. Knowles et al., Desulfonylation of amides using tributyltin hydride, samarium diiodide or zinc/titanium tetrachloride. A comparison of methods, TETRAHEDRON, 56(7), 2000, pp. 979-988
Citations number
44
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
7
Year of publication
2000
Pages
979 - 988
Database
ISI
SICI code
0040-4020(20000211)56:7<979:DOAUTH>2.0.ZU;2-W
Abstract
Deprotection of N-sulfonylated amides can be achieved by reaction with Bu3S nH, SmI2 or TiCl4/Zn. All three methods gave good yields (typically >60%) w hen using N-benzoyl or related amides while the corresponding N-acetyl deri vatives proved to be inert to deprotection under the same reaction conditio ns. The mechanistic implications of this are discussed. (C) 2000 Elsevier S cience Ltd. All rights reserved.