Thiolation of Pyridine-2-sulfonamides using Magnesium Thiolates

Abstract

The thiolation of pyridine-2-sulfonamides using magnesium thiolates is reported. The ortho-functionalizations of these sulfonamides using TMPMgCl·LiCl (TMP = 2,2,6,6-tetramethylpiperidyl) followed by electrophilic quenching produced a range of 3-functionalized pyridine-2-sulfonamides, which were subsequently converted into the corresponding thioethers. Finally, symmetric or asymmetric diorganodisulfides were employed as electrophiles in a one-pot ortho-functionalization–thiolation procedure, leading to pyridine 2,3-disubstituted dithioethers.