49806-13-5Relevant articles and documents
Sulfonyl Fluoride Synthesis through Electrochemical Oxidative Coupling of Thiols and Potassium Fluoride
Laudadio, Gabriele,Bartolomeu, Aloisio De A.,Verwijlen, Lucas M. H. M.,Cao, Yiran,De Oliveira, Kleber T.,No?l, Timothy
supporting information, p. 11832 - 11836 (2019/08/26)
Sulfonyl fluorides are valuable synthetic motifs for a variety of applications, among which sulfur(VI) fluoride exchange-based "click chemistry" is currently the most prominent. Consequently, the development of novel and efficient synthetic methods to access these functional groups is of great interest. Herein, we report a mild and environmentally benign electrochemical approach to prepare sulfonyl fluorides using thiols or disulfides, as widely available starting materials, in combination with KF, as an inexpensive, abundant and safe fluoride source. No additional oxidants nor additional catalysts are required and, due to mild reaction conditions, the reaction displays a broad substrate scope, including a variety of alkyl, benzyl, aryl and heteroaryl thiols or disulfides.
ALKANESULFONYLATION. XIII. SOLVATION EFFECTS OF THE SOLVENT ON THE COMPETING MECHANISMS OF ALKANESULFONYLATION OF PHENOL UNDER CONDITIONS OF CATALYSIS BY TERTIARY AMINES
Bezrodnyi, V. P.,Lyashchuk, S. N.,Skrypnik, Yu. G.
, p. 1128 - 1132 (2007/10/02)
Change in the nature of the solvent leads to a significant change in the ratio of the competing mechanisms in alkanesulfonylation, i.e., the sulfene (1a) and general base catalysis (1b).The most important role here is played by the polarity of the medium, and with increase in the polarity the predominant path changes from (1b) to (1a).In the case of mechanism (1b) the effects of specific solvation show up more strongly than for mechanism (1a).This is due to differences in the structure of the transition states.A quantitative assessment of the solvation effects on the competing paths (1a,b) is given.
ALKANESULFONYLATION REACTIONS. X. EFFECT OF THE STRUCTURE OF THE ALKANESULFONYL HALIDE ON THE FORMATION OF PHENYLALKANESULFONATES CATALYZED BY TRIETHYLAMINE
Bezrodnyi, V. P.,Skrypnik, Yu. G.
, p. 1660 - 1665 (2007/10/02)
The kinetics of the reactions of methane-, propane-, isopropane-, cyclohexane, and phenylmethanesulfonyl chlorides and propanesulfonyl bromide with phenol in the presence of triethylamine in benzene at 30 deg C were investigated by GLC and potentiometric
