Sulfur-Phenolate Exchange As a Fluorine-Free Approach to S(VI) Exchange Chemistry on Sulfonyl Moieties
Alyssa F. J. van den Boom, Muthusamy Subramaniam, Han Zuilhof
Abstract
SuFEx chemistry has recently evolved as next-generation click chemistry. However, in most SuFEx syntheses, additional reagents/catalysts and carefully controlled conditions are still needed. Here, we aim to further generalize S(VI) exchange chemistry, using 4-nitrophenyl phenylmethanesulfonate as example, in which the nitrophenolate group is exchanged for a wide range of (substituted) phenols and alkyl alcohols. Quantitative yields were reached within 10 min under ambient conditions and required only filtering through silica as workup.
Topics & Concepts
ChemistrySulfonylReagentAlkylPhenolsSulfurFluorineOrganic chemistryCatalysisCombinatorial chemistryClick Chemistry and ApplicationsChemical Synthesis and AnalysisSulfur-Based Synthesis Techniques