Fluorosulfonyl radicals: new horizons for the synthesis of sulfonyl fluorides

Abstract

Sulfonyl fluorides are found widespread applications in organic synthesis, chemical biology, drug discovery and materials science. Compared with current methods, direct flurosulfonylation with fluorosulfonyl radical has emerged as a concise...

Synthetic strategies for fluorosulfonylated compounds: application to click chemistry reactions

“…Direct fluorosulfonylation of alkenes, bypassing the use of installed FSO 2 -containing hubs, has been lately developed, especially by radical methodologies. 36…”

“…33,35 Radical synthetic procedures to obtain fluorosulfonylated aliphatic compounds have very recently been reviewed. 36,37 The extraordinary progress in the past few years on the chemistry of sulfonyl fluorides is driven by the SuFEx chemistry which represents one of the most significant click reactions, with relevance in numerous fields and research areas. 38…”

“…33,35 Radical synthetic procedures to obtain fluorosulfonylated aliphatic compounds have very recently been reviewed. 36,37 The extraordinary progress in the past few years on the chemistry of sulfonyl fluorides is driven by the SuFEx chemistry which represents one of the most significant click reactions, with relevance in numerous fields and research areas. 38 We next examine, from the organic chemistry perspective, the catalytic syntheses of (hetero)aromatic-, alkyl-, alkenyl-, and alkynyl-sulfonyl fluorides and β-keto-sulfonyl fluorides and the syntheses of compounds with N-SO 2 F and O-SO 2 F bonds, illustrating examples of their SuFEx chemistry and other ancillary functional group reactivity.…”

Aryl sulfonyl fluoride synthesisviapalladium-catalyzed fluorosulfonylation of aryl thianthrenium salts

“…The growing demand for various aryl sulfonyl fluorides has led to an increasing emphasis on the development of novel and efficient synthetic methods. 3 The conventional synthetic approaches rely on F–Cl exchange of the corresponding arenesulfonyl chlorides 1 a ,4 (Fig. 1a) or oxidative fluorination of thiols and their derivatives 5 (Fig.…”

Selective Fluorosulfonylation of Thianthrenium Salts Enabled by Electrochemistry

“…Arguably, their special utility for click chemistry via fluoride exchange (SuFEx) has further fueled their use (Figure A) . To this end, developing novel yet practical methods for their facile synthesis starting from versatile substrates is of interest . From the viewpoint of bond construction, known methods for accessing these compounds can be roughly classified into three approaches: (1) direct forging of the S–F bond via fluorination of S-containing substrates (such as sulfonyl chlorides, sulfonyl hydrazides, thiols or disulfides, sulfinate intermediates formed via two-step protocols through transition metal-catalyzed cross couplings, and sodium sulfinic) with F – or F + reagents, (2) construction of X–S (X = C, O, or N) bonds using diverse sulfonyl fluoride hubs; and (3) formation of C–S and S–F bonds simultaneously via three-component reactions .…”