Synthetic strategies for fluorosulfonylated compounds: application to click chemistry reactions

Abstract

The syntheses and applications of fluorosulfonylated organic compounds have flourished in the last ten years due to their versatility to participate in click chemistry (SuFEx) reactions. Also, organic architectures that combine the SO2F group and other ancillary functional moieties such as olefins, alkynes, etc. (i.e.: bis-electrophiles) have augmented the applications and diversity of the end compounds. To this effect, the association of an alkyne functionality and the SuFExable group within one structure has been shown to encompass two-in-one click chemistry sequential protocols with the aim of building on the diversity of scaffolds by two consecutive click processes. We next examine the syntheses of (hetero)aromatic-, alkyl-, alkenyl-, and alkynyl-sulfonyl fluorides and β-keto-sulfonyl fluorides and the syntheses of compounds bearing N-SO2F and O-SO2F bonds through diverse catalytic methods, illustrating examples of their SuFEx click chemistry and other ancillary functional group reactivity.