高价碘试剂促进的N-芳基磺酰胺类化合物脱芳基反应

Hypervalent Organoiodine Promoted Dearylation Reaction of N-Aryl Sulfonamides

通过高选择性惰性磺酰胺芳基C—N键裂解反应,发展了一种Dess-Martin氧化剂(DMP)促进的N-芳基磺酰胺的脱芳基的方法.该无金属参与的反应在温和的条件下进行,可提供各种在生物学上有重要应用价值的伯磺酰胺类化合物,其中某些磺酰胺使用传统的氨解和水解方法难以获得.这一简单有效的脱芳基反应可在无金属催化剂条件下使芳基作为磺酰胺类化合物的氨基保护基.

An efficient Dess-Martin periodinane(DMP)-promoted dearylation of N-arylsulfonamides was developed through a highly selective oxidative cleavage of the inert C(aryl)-N bonds in secondary sulfonamides while leaving the S-N bond unchanged.This metal-free reaction proceeds under mild conditions and provides access to various biologically important primary sulfonamides,some of which are otherwise unattainable using conventional aminolysis and hydrolysis methods.The concise and efficient dearylation reaction provides the use of an aryl group as a removable protecting sulfonamide group under metal catalyst-free conditions.