A rapid access to aliphatic sulfonyl fluorides

Abstract

The past few years have witnessed a fast-growing research interest on the study of sulfonyl fluorides as reactive probes in chemical biology and molecular pharmacology, which raises an urgent need for the development of effective synthetic methods to expand the toolkit. Herein, we present the invention of a facile and general approach for the synthesis of aliphatic sulfonyl fluorides via visible-light-mediated decarboxylative fluorosulfonylethylation. The method is based on abundant carboxylic acid feed stock, applicable to various alkyl carboxylic acids including primary, secondary, and tertiary acids, and is also suitable for the modification of natural products like amino acids, peptides, as well as drugs, forging a rapid, metal-free approach to build sulfonyl fluoride compound libraries of considerable structural diversity. Further diversification of the SO 2 F-containing products is also demonstrated, which allows for access to a range of pharmaceutically important motifs such as sultam, sulfonate, and sulfonamide.

The Emerging Applications of Sulfur(VI) Fluorides in Catalysis

“…In 2019, Liao and co-workers reported a photocatalyzed radical-based method for the synthesis of aliphatic sulfonyl fluorides. 65 They postulated the mechanism shown in Scheme 18 . Under irradiation of blue LED light, Eosin Y–Na 2 is excited and reduced by the Hantzsch ester.…”

Emerging Building Blocks for Medicinal Chemistry: Recent Synthetic Advances

“…[180] The list of nucleophiles used in the Michael reactions with alkenyl sulfonyl fluorides include aromatic [291] or aliphatic [309] amines, azide, [164] triazoles, [286] thiols or sulfinates, [291] HP(O)Me 2 , [336] active methylene compounds, [291] and pyrroles. [180] Among the CÀ C bond-forming reactions, visible-lightpromoted radical additions to ESF (39) should be outlined, such as decarboxylative addition of NHPI redox-active esters 9, Scheme 34) [337] or Mn 2 (CO) 10 -catalyzed reductive addition of alkyl iodides. [338] Both methods provided a great scope of biand polyfunctional sulfonyl fluoride building blocks 59 with a remarkable functional group tolerance to and were suitable for the late-stage functionalization.…”

Inhomogeneous superconductivity and quasilinear magnetoresistance at amorphous LaTiO3/SrTiO3 interfaces

“…At higher carrier densities (above 75 V), the in-plane MR showed a decrease, indicating an additional contribution which saturates in high fields. A connection between a non-trivial negative in-plane MR and a linear out-of-plane MR was actually observed in work on thin films of the Dirac semimetal Cd 3 As 2 [49], and in electron doped GaAs quantum wells [50]. In both cases, the macroscopic disorder is argued to be the origin of such behavior of MR. Additional support for this scenario in our samples is that the quasilinear MR develops in the region where high and low-mobility carriers have very similar carrier concentration as shown in figure 4(a), and even appear to cross.…”