A fluorous-tagged, acid-labile protecting group for the synthesis of carboxamides and sulfonamides

J Comb Chem. 2004 Jul-Aug;6(4):611-22. doi: 10.1021/cc0499338.

Abstract

A new acid-labile, fluorous-tagged protecting group that facilitates the preparation of carboxamides and sulfonamides by parallel solution-phase synthesis is introduced. Its use is exemplified by the preparation of a 27-member library of biaryl sulfonamides and an 18-member library of biaryl carboxamides. Intermediates were purified by solid-phase extraction over reversed-phase fluorous silica gel to afford library members in high yields and purities (>95%) without the need for column chromatographic purification.