81329-98-8

Upstream product

• 592-41-6 1-hexene 
• 70-55-3 toluene-4-sulfonamide 
• 80696-29-3 (S)-(+)-2-Amino-1-hexanol 
• 98-59-9 p-toluenesulfonyl chloride 
• 21754-55-2 L-norleucine methyl ester 
• 327-57-1 L-Norleucine 
• 87601-68-1 (S)-2-tosylamino-hexyl 4-toluenesulfonate 
• 68107-05-1 1-Methyl-pentylamin 
• 626-93-7 n-hexan-2-ol 
• 110-62-3 pentanal 

Downstream Products

• 81330-01-0 cis-N-(p-toluenesulfonyl)-2,5-dimethylpyrrolidine 
• 123993-97-5 trans-N-(p-toluenesulfonyl)-2,5-dimethylpyrrolidine 
• 101689-10-5 (S)-3,3,3-Trifluoro-2-methoxy-N-((R)-1-methyl-pentyl)-2-phenyl-propionamide 
• 101689-10-5 3,3,3-Trifluoro-2-methoxy-N-((R)-1-methyl-pentyl)-2-phenyl-propionamide 
• 169268-97-7 (+/-)-tert-butyl hex-5-en-2-ylcarbamate 

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.

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.

Stereoinversion of Unactivated Alcohols by Tethered Sulfonamides

The direct, catalytic substitution of unactivated alcohols remains an undeveloped area of organic synthesis. Moreover, catalytic activation of this difficult electrophile with predictable stereo-outcomes presents an even more formidable challenge. Described herein is a simple iron-based catalyst system which provides the mild, direct conversion of secondary and tertiary alcohols to sulfonamides. Starting from enantioenriched alcohols, the intramolecular variant proceeds with stereoinversion to produce enantioenriched 2- and 2,2-subsituted pyrrolidines and indolines, without prior derivatization of the alcohol or solvolytic conditions.

Triiodide-Mediated δ-Amination of Secondary C?H Bonds

The Cδ?H amination of unactivated, secondary C?H bonds to form a broad range of functionalized pyrrolidines has been developed by a triiodide (I3?)-mediated strategy. By in situ 1) oxidation of sodium iodide and 2) sequestration of the transiently generated iodine (I2) as I3?, this approach precludes undesired I2-mediated decomposition which can otherwise limit synthetic utility to only weak C(sp3)?H bonds. The mechanism of this triiodide-mediated cyclization of unbiased, secondary C(sp3)?H bonds, by either thermal or photolytic initiation, is supported by NMR and UV/Vis data, as well as intercepted intermediates.

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.

Inter- and intramolecular hydroamination of unactivated alkenes catalysed by a combination of copper and silver salts: The unveiling of a Bronstedt acid catalysis

The combined use of a copper halide, a silver salt and a phosphane ligand was applied for the catalysis of inter- and intramolecular hydroamination of alkenes. The reactions of unactivated olefins with nitrogen substrates were investigated. Mechanistic investigations demonstrated that the catalytic system generated a Bronsted acid which appeared to be the prominent catalytic species. Copyright

Efficient C-N bond formations catalyzed by a proton-exchanged montmorillonite as a heterogeneous Bronsted acid

Nucleophilic addition of sulfonamides and carboxamides to simple alkenes proceeded smoothly using a proton-exchanged montmorillonite catalyst. The spent catalyst was recovered easily from the reaction mixture and was reusable at least five times without any loss of activity. The unique acidity of the proton-exchanged montmorillonite (H-mont) catalyst was found to be applicable to additional reactions: substitution of hydroxyl groups of alcohols with amides and anilines.

SYNTHESIS OF THE RACEMIC FORM OF (Z)-1,17-DIAMINOOCTADEC-9-ENE, AN ALIPHATIC DIAMINE FROM COCCINELLIDAE. DETERMINATION OF THE ABSOLUTE CONFIGURATION OF THE (+)-NATURALLY-OCCURRING ANTIPODE

The total synthesis of the title compound (1) has been achieved.Also reported is the use of lanthanide induced shifts in 1H NMR spectroscopy to assign the absolute configuration of the α-carbon atom in chiral primary α-methylalkylamines.Application of this empirical method to natural (+)-1 shows that it has the R-configuration at C-17.

Sulphonamidomercuriation of Olefins and Subsequent Reductive Demercuriation or Bromodemercuriation

The addition of toluene-p-sulphonamide to olefins in the presence of anhydrous mercury(II) nitrate and subsequent sodium borohydride reduction leads to the corresponding N-alkylsulphonamides.The sulphonamidomercuriation-demercuriation of 1,4- and 1,5-dienes yields saturated nitrogen-containing heterocycles.A possible mechanism for the stereoselective synthesis of cis-2,5-dimethyl-N-tosylpyrrolidine is proposed.The treatment of the intermediate organomercurials, isolated as the sodium salts of their bromomercurio derivatives, with bromine gives the corresponding 2-bromoalkylsulphonamides through a regiospecific bromodemercuriation process.

Sulphonamidomercuration; a New Method for Amination of Olefins

The addition of toluene-p-sulphonamide to olefins in the presence of anhydrous mercury(II) nitrate and subsequent sodium borohydride reduction leads to the corresponding N-alkyl-sulphonamides; the use of 1,4- and 1,5-dienes yields saturated nitrogen-containing heterocycles, the synthesis of tosylated pyrrolidine being a stereoselective reaction.