14894-42-9

Upstream product

• 124-40-3 dimethyl amine 
• 1939-99-7 benzenesulfonyl chloride 
• 74-88-4 methyl iodide 
• 108-86-1 bromobenzene 
• 918-05-8 N,N-dimethylmethanesulfonamide 
• 14346-88-4 1,3-Bis--3-phenyl-propen-(1) 
• 51-80-9 bis-(dimethylamino)methane 
• 108-90-7 chlorobenzene 

Downstream Products

• 93152-30-8 3-morpholin-4-yl-1-phenyl-propane-1-sulfonic acid dimethylamide 
• 128622-77-5 <1-Hydroxy-4-t-butyl-cyclohexyl>-phenylmethanesulfonic acid N,N-dimethylamide 
• 128622-78-6 <1-Hydroxy-4-t-butyl-cyclohexyl>-phenylmethanesulfonic acid N,N-dimethylamide 
• 858005-58-0 (3-nitro-phenyl)-methanesulfonic acid dimethylamide 

Relevant academic research and scientific papers

Palladium-Catalyzed α-Arylation of Methyl Sulfonamides with Aryl Chlorides

A palladium-catalyzed α-arylation of sulfonamides with aryl chlorides is presented. A Buchwald-type pre-catalyst formed with Kwong’s indole-based ligand enabled this transformation to be compatible with a large variety of methyl sulfonamides and aryl chlorides in good to excellent yields. Importantly, under the optimized reaction conditions, only mono-arylated products were observed. This method has been applied to the efficient synthesis of sumatriptan, which is used to treat migraines. (Figure presented.) .

A useful Pd-catalyzed Negishi coupling approach to benzylic sulfonamide derivatives

(Chemical Equation Presented) A mild catalytic system to access diversely functionalized benzylic sulfonamides has been developed. Palladium-catalyzed α-arylation by Negishi cross-coupling of sulfonamide-stabilized anions and a wide range of aryl iodides, bromides, and triflates constitutes a practical strategy for the synthesis of various benzylic sulfonamides.

Synthesis of α-fluorosulfonamides by electrophilic fluorination

(Chemical Equation Presented) α-Fluorosulfonamides were prepared by electrophilic fluorination of tertiary sulfonamides using N- fluorobenzenesulfonimide as fluorinating agent and utilizing the dimethoxybenzyl group (DMB) as a new sulfonamide protecting g

Secondary Reactions of Sulfenes from Sulfonyl Chlorides and Tertiary Amines. 2. Formation of Episulfones, Sulfonylsulfene - Amine S,N-Adducts and Chlorsulfines from Primary Sulfonyl Chlorides and Tertiary Amines

The reaction of primary sulfonyl chlorides 1b-m with the tertiary amine bases quinuclidine, DABCO, Me3N, Et3N, Bu3N, EtiPr2N, and 1,2,2,6,6-pentamethylpiperidine is studied in acetonitrile solution between -40 and 80 deg C.The 2,3-dialkylthiirane 1,1-dioxides 4 (trans/cis > 1) and the alkenes 5 1> are obtained in high yields with Et3N at -40 deg C.The stereochemistry is influenced by the amine base B in the ring-closure reaction and partially by epimerization of the episulfones 4.Hindered bases favor the cis, β-branched sulfonyl chlorides the trans isomer.Competing formation of the sulfonylsulfene - amine S,N-adducts 7 is only observed with quinuclidine, DABCO, and Me3N, which are also the most active amines in the epimerization of the cis-2,3-diarylthiirane 1,1-dioxides 4.Methanesulfonyl chloride (1a) yields the mesylsulfene - amine S,N-adducts 7a with Me3N and Et3N in MeCN, but thiirane 1,1-dioxide (4a) with EtiPr2N in MeCN or with Et3N in Et2O.Formation of chlorosulfines 10 is favored by higher temperature (T > 20 deg C), hindered amine bases and β-branched sulfonyl chlorides.Isolation of 10g and 10h in high yields shows that tert-alkylchlorosulfines are rather stable sulfines.

Secondary Reactions of Sulfenes from Sulfonyl Chlorides and Tertiary Amines, 1. - On the Competing Formation of Sulfene-Trialkylamine S,N- and C,N-Adducts

Phenylmethanesulfonyl chloride (1 a) reacts with an excess oif triethylamine in acetonitrile solution at -40 deg C to give stilbene episulfone (9 a, 95percent) via the phenylsulfene-triethylamine S,N-adduct 5 ah.With trimethylamine and quinuclidine the yield of stilbene is reduced by the additional formation of (benzylsulfonyl)phenylsulfene-amine S,N-adducts 11 ag and 11 ae and C,N-adducts 15 ag and 15 ae which was proven by reaction with dimethylamine to 16 and by hydrolysis to 17-19, respectively. 1 d reacts with triethylamine yielding 94percent of α-chloro sulfones 4 d and 6 d via pentamethylenesulfene-triethylamine S,N-adduct 5 dh, with trimethylamine, however, C,N-adduct 12 dg is obtained which is easily oxidized to 20 dg (47percent).The air-sensitive dimethylsulfene-trimethylamine C,N-adduct 12 cg was isolated and characterized.