Phase transfer catalysis in the tert-butyloxycarbonylation of alcohols, phenols, enols, and thiols with di-tert-butyl dicarbonate

Abstract

It is shown that the tert-butyloxycarbonylation of phenols, alcohols, enols, and thiols can be accomplished by reaction of these functionalities with di-tert-butyl dicarbonate under phase transfer conditions. The reactions proceed in high yield and can also be used for the introduction of t-BOC groups onto functionalized polymer backbones such as novolac or poly(p-hydroxystyrene). In addition, a study is made of the selectivity towards tert-butyloxycarbonylation of various polyfunctional compounds.