Silicon‐Free SuFEx Reactions of Sulfonimidoyl Fluorides: Scope, Enantioselectivity, and Mechanism
Dong‐Dong Liang, Dieuwertje E. Streefkerk, Daan Jordaan, Jorden Wagemakers, Jacob Baggerman, Han Zuilhof
Abstract
SuFEx reactions, in which an S-F moiety reacts with a silyl-protected phenol, have been developed as powerful click reactions. In the current paper we open up the potential of SuFEx reactions as enantioselective reactions, analyze the role of Si and outline the mechanism of this reaction. As a result, fast, high-yielding, "Si-free" and enantiospecific SuFEx reactions of sulfonimidoyl fluorides have been developed, and their mechanism shown, by both experimental and theoretical methods, to yield chiral products.
Topics & Concepts
MoietyMechanism (biology)Enantioselective synthesisYield (engineering)ChemistrySilylationReaction mechanismScope (computer science)SiliconCatalysisCombinatorial chemistryPhenolOrganic chemistryComputational chemistryMaterials scienceComputer sciencePhysicsProgramming languageQuantum mechanicsMetallurgyClick Chemistry and ApplicationsFluorine in Organic ChemistryChemical Synthesis and Analysis