66898-24-6

Upstream product

• 873-55-2 sodium benzenesulfonate 
• 110-58-7 n-Pentylamine 
• 98-10-2 benzenesulfonamide 
• 71-41-0 pentan-1-ol 
• 98-09-9 benzenesulfonyl chloride 
• 80-17-1 benzenesufonyl hydrazide 
• 1616490-49-3 C₁₈H₂₃NO₂S 
• 111-26-2 hexan-1-amine 

Downstream Products

• 66897-50-5 N-(2-Chloro-benzoyl)-N-pentyl-benzenesulfonamide 
• 103085-22-9 2-ethyl-1-(phenylsulfonyl)pyrrolidine 
• 103085-23-0 1,1-dioxo-2-hexyl-1,2-benzothiazetidine 

Relevant academic research and scientific papers

N -Alkylation of organonitrogen compounds catalyzed by methylene-linked bis-NHC half-sandwich ruthenium complexes

An efficient ruthenium-catalyzed N-alkylation of amines, amides and sulfonamides has been developed employing novel pentamethylcyclopentadienylruthenium(ii) complexes bearing the methylene linked bis(NHC) ligand bis(3-methylimidazol-2-ylidene)methane. The

AEROBIC OXIDATIVE SYNTHESIS OF SULFONAMIDE USING Cu CATALYST

The present invention relates to a method for oxidative synthesis of sulfonamides using copper catalysts. , Oxygen (O) is used. 2 The oxidative synthesis of sulfonamides (1) comprises reacting a 2 th or sulfonyl hydrazide primary amine with a sulfonyl hydrazide (sulfonamide) with a copper catalyst on a solvent under the conditions in which the sulphonamide is fed. The oxidation coupling of the present invention showed extensive substrate ranges in an amine comprising a 2 primary amine, 1 primary amine and amine hydrochloride salt. It is worth notable that non-reactive aliphatic sulfonyl hydrazides in previously reported anaerobic systems can be used for the aerobic oxidation coupling of the present invention. The oxidation coupling of the present invention has been more effective on large scale.

Photoredox-mediated mono- And difluorination of remote unactivated methylene C(sp3)-H bonds of N-alkyl sulfonamides

A photoredox-mediated δ-C(sp3)-H fluorination of sulfonyl-protected primary alkylamines with Selectfluor is developed. The reaction can proceed in excellent monofluorination selectivity for amine substrates without α substituent. For α-substituted substrates, a slightly modified reaction conditions with two rounds of operation gives the δ,δ-difluorination products in good yield. Mechanistic studies suggest SET oxidation of sulfonamide group directly generates the key sulfonamide N radical intermediate, which triggers a 1,5-HAT process to form the δ alkyl radical.

Efficient and Practical Synthesis of Sulfonamides Utilizing SO2 Gas Generated on Demand

A simple and practical protocol was developed for the synthesis of sulfonamides by reacting organometallic reagents with SO2 gas generated on demand. SO2 was generated from readily available reagents safely in a highly contained and controlled fashion. The protocol allows the synthesis of sulfonamides without using either atom-inefficient SO2 surrogates or a SO2 cylinder that requires stringent storage regulations in the laboratory. The protocol was successfully applied to the synthesis of sildenafil.

Photoinduced site-selective C(sp3)-H chlorination of aliphatic amides

Herein, we report a new photochemical method for C(sp3)-H chlorination of amides which employs tert-butyl hypochlorite as the chlorinating agent and a household compact fluorescent lamp as the light source. The reaction proceeds via N-heterocyclic carbene SIPr·HCl-promoted N-H chlorination and subsequent photoinduced Hofmann-L?ffler-Freytag chlorine atom transfer. The latter process is facilitated by (diacetoxyiodo)benzene. This protocol exhibits a broad scope and is suitable for site-selective chlorination of methyl hydrogen as well as methylene and methine hydrogen.

Copper-Catalyzed Amide Radical-Directed Cyanation of Unactivated Csp3-H Bonds

A method for site-selective intermolecular δ/?-Csp3-H cyanation of aliphatic sulfonamides is developed using TsCN as the cyanating reagent, catalyzed by a Cu(I)/phenanthroline complex. The mild, expeditious, and modular protocol allows efficient remote Csp3-H cyanation with good functional group tolerance and high regioselectivity. Mechanistic studies indicate that the reaction might proceed through a Cu(I)-mediated N-F bond cleavage to generate an amidyl radical, 1,5-HAT, and cyano group transfer of the resulting carbon radical with TsCN.

Cu-catalyzed aerobic oxidative synthesis of sulfonamides from sulfonyl hydrazides and amines

An environmentally friendly route for sulfonamides has been developed. The oxidative coupling of sulfonyl hydrazides and amines was catalyzed by CuBr2 to produce various sulfonamides with the water and nitrogen gas as byproducts. Preliminary experiments revealed that the sulfonyl radical is likely to be involved in the reaction mechanism.

Metal-free direct construction of sulfonamides via iodine- mediated coupling reaction of sodium sulfinates and amines at room temperature

A simple, practical, and metal-free protocol has been developed for the synthesis of sulfonamides from sodium sulfinates and various amines through an iodine-mediated SN bond formation reaction at room temperature. This green reaction is cost-effective, operationally straightforward, and especially proceeds under very mild conditions to afford the target products in good to excellent yields (up to 98%).

Oxidative debenzylation of N-benzyl amides and O-benzyl ethers using alkali metal bromide

The oxidative debenzylation of N-benzyl amides and O-benzyl ethers was promoted with high efficiency by a bromo radical formed through the oxidation of bromide from alkali metal bromide under mild conditions. This reaction provided the corresponding amides from N-benzyl amides and carbonyl compounds from O-benzyl ethers in high yields.

REGIOSPECIFIC OXIDATIVE CYCLIZATION OF N-METHYLSULFONYLAMINES INTO PYRROLIDINES

In the framework of the approach to remote oxidative functionalization of organic compounds of various classes, which is currently under exploration by us and which is based on reactions of element-centred free radicals, the regiospecific oxidative cyclization of N-methylsulfonylalkylamines 3 into N-methylsulfonylpyrrolidines 4 has been accomplished.The more facile isomerisation of intermediate sulfonamidyl radicals 8 with 1,5-H shift in comparison with their carboxamidyl analogues 16 is, in our opinion, the chemical proof of different electronic configurations of radicals 8 (? structure) and 16 (predominantly ? structure) generated under identical conditions using Na2S2O8-CuCl2 system.