N-Sulfonylbenzotriazoles as Advantageous Reagents for C-Sulfonylation

Abstract

[Structure: see text]. Reactions of readily available N-(alkyl-, aryl-, and heteroarylsulfonyl)benzotriazoles 3a-h with diverse nitriles, reactive heteroaromatics, alkylheteroaromatics, sulfones, and esters produced alpha-cyanoalkyl sulfones 5a-i, sulfonylheteroaromatics 7a-e, alpha-(sulfonylalkyl)heterocycles 9a-f, alpha-sulfonylalkyl sulfones 11a-g, and esters of alpha-sulfonyl acids 14a-c, respectively, in synthetically useful to excellent yields. The results represent the first examples of the successful application of sulfonylazoles for C-sulfonylation.

Organolithium-Mediated Postfunctionalization of Thiazolo[3,2-c][1,3,5,2]oxadiazaborinine Fluorescent Dyes

“…Notably, analogically to cyanation, sulfonation reaction did not occur with electrophilic halogenide (phenylsulfonyl chloride, entry 12 in Table 1 ); chloro-substituted product 2a in 65% yield was isolated in this case. Compound 2j with sulfone group was successfully obtained in 80% yield using phenylsulfonyl-benzotriazole ( Bt-SO 2 Ph ) 32 as the electrophile. The synthesis of Bt-SO 2 Ph was efficiently realized by sulfonation of unsubstituted benzotriazole with phenylsulfonyl chloride in basic conditions ( Scheme 1 ).…”

“…This compound was obtained using a modified literature procedure. 32 A solution of benzotriazole (1.00 g, 8.39 mmol) and pyridine (1.5 equiv, 1.01 mL, 12.59 mmol) in dry toluene (12 mL) was cooled to 0 °C. Then, a solution of phenylsulfonyl chloride (1.2 equiv, 1.29 mL, 10.07 mmol) in toluene (3 mL) was added dropwise.…”

A Facile and Eco-Friendly Method for the Synthesis of Sulfonamide and Sulfonate Carboxylic Acid Derivatives—X-ray Structure, Hirshfeld Analysis and Spectroscopic Characterizations

“…In addition, all the reported methods use organic solvents such as dichloromethane and/or toxic activating agents such as thionyl chloride for the synthesis of sulfonamides. Furthermore, multi-step synthesis methods that are time-consuming for purifications are usually needed [20].…”

Convenient synthesis of sulfonamides from amines and p‐toluene sulfonyl chloride mediated by crosslinked poly(4‐vinylpyridine)

“…Although many efforts have been made towards the preparation of novel sulfonamides,11–20 the conventional synthesis involves the reaction of amino compounds with sulfonyl chlorides in the presence of a base or catalyst 21–25. Alternatively sulfonamides can be obtained by reacting sulfinic acid salts with an electrophilic nitrogen source such as hydroxylamine‐ O ‐sulfonic acid,26 or bis(2, 2, 2‐trichloroethyl) azodicarboxylate,27 by reacting sulfonic acid with isocyanides 28.…”