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Upstream product

• 13707-45-4 N-benzylidene-4-chlorobenzenesulfonamide 
• 143-66-8 sodium tetraphenyl borate 
• 98-64-6 4-Chlorobenzenesulfonamide 
• 101-81-5 Diphenylmethane 
• 91-01-0 1,1-Diphenylmethanol 
• 574-42-5 benzhydryl ether 

Relevant academic research and scientific papers

Reaction Route and Mechanism of the Direct N-Alkylation of Sulfonamides on Acidic Mesoporous Zeolite β-Catalyst

Development of highly active heterogeneous catalysts with strong acidity and mesoporous structure is a highly attractive strategy for organic synthesis. In this study, a mesoporous zeolite beta (HBeta-M) with bulky particle size and strong acidity was synthesized and used in the direct N-alkylation of sulfonamides with alcohols. The strongly acidic HBeta-M had a higher intrinsic activity with initial turnover frequency of 11 × 10-2 s-1 than those of H-form mordenite nanosheets (3.3 × 10-2 s-1) and montmorillonite (4.0 × 10-2 s-1) catalysts. The experiment and characterization results demonstrate that there are two parallel reaction routes on the acidic catalysts. One route is the reaction of benzhydrol with p-toluenesulfonamide (route I). Another route is the reaction of dibenzhydryl ether, arising from route I, with p-toluenesulfonamide (route II), which is found in this work. The reaction rate of route I (13 × 10-3 mol kg-1 s-1) was higher than that of route II (9.8 × 10-3 mol kg-1 s-1) on HBeta-M, but route II predominantly contributed to the formation of the target product with high selectivity. Hereby, a complete reaction mechanism is proposed in this work.

Selective catalytic Hofmann: N -alkylation of poor nucleophilic amines and amides with catalytic amounts of alkyl halides

Using only catalytic amounts of alkyl halides in the reactions of poor nucleophilic amines/amides and alcohols led to a selective Hofmann N-alkylation reaction catalytic in alkyl halides, providing a practical and efficient method for the practical synthesis of mono- or di-alkylated amines/amides in high selectivities. This new method avoids the use of large amounts of bases, alkyl halides, and solvents, and generates water as the only byproduct. Preliminary mechanistic studies showed that alkyl halides are key intermediates/catalysts regeneratable in the reaction cycle.

Transition-metal-free intermolecular amination of sp3 C-H bonds with sulfonamides

An efficient transition-metal-free intermolecular benzylic amidation with sulfonamides is described. Various valuable nitrogen-containing compounds, including amines, β-chloro amine, amino alcohol, α-, β-amino ester, and N-sulfonyl imine, are generated fr

General and efficient copper-catalyzed amidation of saturated C-H bonds using N-halosuccinimides as the oxidants

(Chemical Equation Presented) We have developed a general and efficient method for copper-catalyzed amidation of saturated C-H bonds under mild conditions, and the used substrates include benzylic reagents, the N,N-dimethylaniline derivatives, the free carboxamides, and sulfonamides. The protocol uses inexpensive and readily available CuBr/N-halosuccinimide (NBS or NCS) as the catalyst/oxidant, so it provides practical applications for synthesis of various amides via C-H activation.

Efficient intermolecular iron-catalyzed amidation of C-H bonds in the presence of n-bromosuccinimide

We have developed an efficient, inexpensive, and air-stable catalyst/oxidant (FeCI2/NBS) system that could efficiently promote amidation of benzylic sp3 C-H bonds in ethyl acetate under mild conditions.

Rhodium-catalyzed phenylation of N-arylsulfonyl aldimines with sodium tetraphenylborate or trimethyl(phenyl)stannane

The rhodium-catalyzed addition reactions of trimethyl(phenyl)stannane and sodium tetraphenylborate to N-phenylsulfonyl aldimines RCH=NSO2Ph (R=alkyl and aryl) provided R(Ph)CHNHSO2Ph in high yields. A cationic and free phosphine complex [Rh(cod)(MeCN)2]BF4 was found to be an efficient catalyst for the addition of PhSnMe3, whereas [Rh(cod)(MeCN)2]BF4/dppb catalyzed the addition of Ph4BNa to various N-sulfonyl aldimines in dioxane at 90°C. The scope and limitations of the reactions, as well as the effect of varying the reaction conditions, are discussed.