19158-31-7

Upstream product

• 110-91-8 morpholine 
• 76625-87-1 bis(phenylmethyl) α-disulfone 
• 1939-99-7 benzenesulfonyl chloride 
• 1697-34-3 4-methanesulfonylmorpholine 
• 108-86-1 bromobenzene 
• 51793-64-7 sodium α-toluenesulfinate 
• 108-90-7 chlorobenzene 
• 16601-40-4 S-benzyl phenyl-methanethiosulfonate 

Downstream Products

• 93019-85-3 4-(phenyl-pyridin-2-yl-methanesulfonyl)-morpholine 
• 71376-53-9 4-(1-phenyl-propane-1-sulfonyl)-morpholine 
• 94907-49-0 4-(4,4-dimethyl-1-phenyl-pentane-1-sulfonyl)-morpholine 
• 93950-78-8 4-(1,2-diphenyl-ethanesulfonyl)-morpholine 
• 71376-54-0 4-(1-phenyl-butane-1-sulfonyl)-morpholine 
• 94801-87-3 4-(3-diethylamino-1-phenyl-propane-1-sulfonyl)-morpholine 
• 71376-55-1 4-([1-phenylbut-3-en-1-yl]sulfonyl)morpholine 
• 71376-63-1 4-(dichloro-phenyl-methanesulfonyl)-morpholine 
• 22456-73-1 4-(nitro-phenyl-methanesulfonyl)-morpholine 
• 71376-64-2 α-chlorobenzyl 4-morpholinyl sulfone 
• 71376-62-0 4-(1-chloro-1-phenyl-propane-1-sulfonyl)-morpholine 
• 88534-33-2 phenyl(morpholinosulfonyl)sulfine 
• 88534-26-3 N-<α-(trimethylsilyl)benzylsulfonyl>morpholine 

Relevant academic research and scientific papers

Sulfinates from Amines: A Radical Approach to Alkyl Sulfonyl Derivatives via Donor-Acceptor Activation of Pyridinium Salts

Synthetically versatile alkyl sulfinates can be prepared from readily available amines, using Katritzky pyridinium salt intermediates. In a catalyst-free procedure, primary, secondary, and benzylic alkyl radicals are generated by photoinduced or thermally induced single-electron transfer (SET) from an electron donor-acceptor (EDA) complex, and trapped by SO2 to generate sulfonyl radicals. Hydrogen atom transfer (HAT) from Hantzsch ester gives alkyl sulfinate products, which are used to prepare a selection of medicinal chemistry relevant sulfonyl-containing motifs.

Process for the Synthesis of Sulfones and Sulfonamides

A one pot single step process is described for the synthesis of a compound, including a labeled compound, containing a sulfonyl functional group comprising the step of mixing together a silane, an SO2 source, an electrophilic compound, an activ

Benzothiazole Sulfinate: A Sulfinic Acid Transfer Reagent under Oxidation-Free Conditions

Sulfinic acids are commonly encountered intermediates found in natural product synthesis and medicinal chemistry. However, because of high reactivity, instability, and harsh reaction conditions, they are difficult to synthesize. Herein we have developed an oxidation-free method to produce sulfinic acids and sulfinate salts using 2-sulfinyl benzothiazole (BTS). We have also demonstrated the synthetic usefulness by developing one-pot syntheses of sulfones and sulfonamides.

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.) .

Palladium-catalyzed benzylic direct arylation of benzyl sulfones with aryl halides

An effective palladium catalyst system for the direct arylation of benzyl sulfones with aryl halides has been developed. The catalytic reaction provides a facile route to diarylmethyl sulfones. The products can be transformed further via desulfonylative functionalization mediated by aluminum compounds.

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.

Palladium-catalysed arylation of sulfonamide stabilised enolates

α-Arylation of methanesulfonamides using palladium catalysis is described. For example, treatment of N-benzyl-N-methylmethanesulfonamide with catalytic Pd(OAc)2 in the presence of sodium tert-butoxide, triphenylphosphine and toluene afforded N-

Preparation of sulfines by alkylidenation of sulfur dioxide using α-silyl carbanions

The synthesis of sulfines 4 from a series of active methylene compounds is described.Deprotonation, followed by silylation, gives the trimethylsilyl compounds 2.Subsequent deprotonation to α-silyl carbanions and treatment with an excess of sulfur dioxide

Substitution Reactions of Alkanesulfonyl Derivatives: Direct Substitution vs. Elimination-Addition Mechanisms in Substitution Reactions of Alkyl α-Disulfones

The reactions of a series of alkyl and aralkyl α-sulfones, RSO2SO2R ( R = Me, n-Bu, i-Pr, ArCH2) with a variety of nucleophiles in aqueous dioxane have been examined.Both rates of reaction and whether a given reaction takes place by an elimination-addition (sulfene intermediate) or a direct substitution (attack of nucleophile on SO2 group of α-sulphone) mechanism have been determined.The great majority of substitution reactions of alkyl α-disulfones take place via an elimination-addition mechanism (eq 3a), with formation of a sulphene from the α-disulphone being rate determining.Only when nucleophile is one, like azide ion, that is weakly basic while still being a good nucleophile is a direct substitution the preferred pathway.Even with azide the reaction pathway changes to elimination-addition when the acidity of the hydrogens on the carbon adjacent to the sulfonyl group is increased sufficiently, as in (PhCH2SO2)2.Comparison of rates of elimination of α-disulphones (R'CH2SO2)2 with rates of base-catalyzed hydrogen exchange of the corresponding trifluoromethyl sulfones R'CH2SO2CF3 indicates that formation of sulfenes from α-disulfones involves either an irreversible E1cB or a very E1cB-like E2 mechanism, a conclusion that is also supported by the observed variation of the rate of elimination of RR'CHSO2SO2R'' with changes in R and R'.Comparison of the behavior of an alkyl α-disulfone with that of the corresponding alkanesulfonyl chloride reveals that changing Y in RCH2SO2Y from RSO2 to Cl causes direct substitution to be able to compete much more effectively with elimination-addition.Kinetic studies show that this arises because, for a given nucleophile, (a) elimination-addition is 5-10 times slower for the alkanesulfonyl chloride than for the α-disulfone while (b) the rate of direct substitution is 5-10 times faster for the sulfonyl chloride.The origin of these rate differences is discussed and explained.