57186-74-0

Upstream product

• 110-83-8 cyclohexene 
• 640-61-9 N-methyl-p-toluenesulfonylamide 
• 62316-86-3 cyclohexyl-methyl-amine; toluene-4-sulfonate 
• 110-82-7 cyclohexane 
• 98-94-2 N,N-dimethyl-cyclohexanamine 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 98-59-9 p-toluenesulfonyl chloride 

Relevant academic research and scientific papers

Iron-Catalyzed Hydroamination and Hydroetherification of Unactivated Alkenes

The hydrofunctionalization of alkenes, explored for over 100 years, offers the potential for a direct, atom-economical approach to value-added products. While thermodynamically favored, the kinetic barrier to such processes necessitates the use of catalysts to control selectivity and reactivity. Modern variants typically rely on noble metals that require different ligands for each class of hydrofunctionalization, thereby limiting generality. This Letter describes a general iron-based system that catalyzes the hydroamination and hydroetherification of simple unactivated olefins.

An approach to C-N activation: Coupling of arenesulfonyl hydrazides and arenesulfonyl chlorides with: Tert -amines via a metal-, oxidant- and halogen-free anodic oxidation

tert-Amines were harnessed to afford arenesulfonyl hydrazides and arenesulfonyl chlorides via a metal-, oxidant- and halogen-free electrochemical oxidative coupling in an undivided cell at RT. This environmentally benign approach afforded a wide spectrum of sulfonamides in satisfactory yields using cheap and renewable Pencil Graphite Electrodes (PGEs).

On the understanding of BF3·Et2O-promoted intra- and intermolecular amination and oxygenation of unfunctionalized olefins

BF3·Et2O was found to be effective for both intra- and intermolecular amination and oxygenation of unfunctionalized olefins. In the presence of 3 equiv. of BF3·Et2O, intramolecular hydroamination of N-(pent-4-enyl)-p-toluenesulfonamides, N-(hex-5-enyl)-p-toluenesulfonamides, intermolecular hydroamination between sulfonamides and cyclohexene, norbornene or styrene, lactonization of pent-4-enoic acid or hex-5-enoic acid compounds and esterification of cyclohexene with different carboxylic acids all proceeded readily, leading to the corresponding amination or oxygenation products in up to 99% isolated yields. Preliminary NMR experiments and DFT calculations suggested that the intramolecular hydroamination reactions proceeded via a sulfonimidic acid intermediate (N=S-OH), and formation of the corresponding Bronsted acid HF or HBF4 was less likely.

Copper-catalyzed intermolecular amidation and imidation of unactivated alkanes

We report a set of rare copper-catalyzed reactions of alkanes with simple amides, sulfonamides, and imides (i.e., benzamides, tosylamides, carbamates, and phthalimide) to form the corresponding N-alkyl products. The reactions lead to functionalization at secondary C-H bonds over tertiary C-H bonds and even occur at primary C-H bonds. [(phen)Cu(phth)] (1-phth) and [(phen)Cu(phth)2] (1-phth2), which are potential intermediates in the reaction, have been isolated and fully characterized. The stoichiometric reactions of 1-phth and 1-phth2 with alkanes, alkyl radicals, and radical probes were investigated to elucidate the mechanism of the amidation. The catalytic and stoichiometric reactions require both copper and tBuOOtBu for the generation of N-alkyl product. Neither 1-phth nor 1-phth2 reacted with excess cyclohexane at 100 C without tBuOOtBu. However, the reactions of 1-phth and 1-phth2 with tBuOOtBu afforded N-cyclohexylphthalimide (Cy-phth), N-methylphthalimide, and tert-butoxycyclohexane (Cy-OtBu) in approximate ratios of 70:20:30, respectively. Reactions with radical traps support the intermediacy of a tert-butoxy radical, which forms an alkyl radical intermediate. The intermediacy of an alkyl radical was evidenced by the catalytic reaction of cyclohexane with benzamide in the presence of CBr4, which formed exclusively bromocyclohexane. Furthermore, stoichiometric reactions of [(phen)Cu(phth)2] with tBuOOtBu and (Ph(Me)2CO) 2 at 100 C without cyclohexane afforded N-methylphthalimide (Me-phth) from β-Me scission of the alkoxy radicals to form a methyl radical. Separate reactions of cyclohexane and d12-cyclohexane with benzamide showed that the turnover-limiting step in the catalytic reaction is the C-H cleavage of cyclohexane by a tert-butoxy radical. These mechanistic data imply that the tert-butoxy radical reacts with the C-H bonds of alkanes, and the subsequent alkyl radical combines with 1-phth2 to form the corresponding N-alkyl imide product.

Recyclable gallium as catalyst precursor for a convenient and solvent-free method for the intermolecular addition of sulfonamides to alkenes

Gallium(III) iodide, which is conveniently formed in situ from gallium and iodine, is a competent catalyst for the inter- and intramolecular addition of p-toluenesulfonamides to alkenes. After each reaction, the metallic gallium can easily be recycled and used for subsequent transformations. Georg Thieme Verlag Stuttgart.

One-Pot synthesis of sulfonamides from primary and secondary amine derived sulfonate salts using cyanuric chloride

A convenient, mild and efficient one-pot synthesis of new sulfonamides is described. The reaction of primary or secondary amine derived sulfonate salts in the presence of cyanuric chloride, triethylamine as base, and anhydrous acetonitrile as solvent at room temperature gives the corresponding sulfonamides in good to excellent yields. Georg Thieme Verlag Stuttgart.

Highly efficient and reusable ionic liquids for the catalyzed hydroamination of alkenes with sulfonamides, carbamates, and carboxamides

SO3H-Functionalized ionic liquids were found to be efficient and reusable catalysts in the hydroamination of sulfonamides, carboxamides, p-nitroaniline and carbamates with nonactivated alkenes. The hydroamination could be performed on a large scale and the acidic ionic liquid catalyst could be reused successfully. Georg Thieme Verlag Stuttgart.

Gold(I)-catalyzed intra- and intermolecular hydroamination of unactivated olefins

Ph3PAuOTf catalyzes efficient intra- and intermolecular hydroamination of unactivated olefins with sulfonamides. Copyright