102992-40-5

Upstream product

• 7242-92-4 exo-2-aminonorbornane 
• 98-88-4 benzoyl chloride 
• 498-66-8 norborn-2-ene 
• 55-21-0 benzamide 
• 211747-63-6 exo-N-bicyclo[2.2.1]heptan-2-yl-4-methylbenzenesulfonamide 
• 936482-38-1 3-benzylamino-3,5-dimethylcyclohexa-1,4-dienecarboxylic acid methyl ester 
• 279-23-2 norbornene 
• 582-61-6 benzoyl azide 
• 65481-69-8 bicyclo[2.2.1]heptan-2-endo-amine hydrochloride 
• 23112-27-8 N-((Z)-1-methyl-3-oxobut-1-enyl)benzamide 
• 936482-29-0 N-((Z)-1,3-dimethylbuta-1,3-dienyl)benzamide 

Downstream Products

• 111013-45-7 5-exo-acetoxy-2-exo-benzoylamino norbornane 
• 111013-45-7 5-exo-acetoxy-2-endo-benzoylamino norbornane 
• 105512-48-9 N-((1R,2R,4R,5S)-5-Hydroxy-bicyclo[2.2.1]hept-2-yl)-benzamide 
• 105512-48-9 N-((1S,2R,4S,5R)-5-Hydroxy-bicyclo[2.2.1]hept-2-yl)-benzamide 

Relevant academic research and scientific papers

Heteropoly acids: a green and efficient heterogeneous Br?nsted acidic catalyst for the intermolecular hydroamination of olefins

Intermolecular hydroamination of non-activated olefins with amides and benzyl carbamate proceeds efficiently in the presence of environmentally benign silicotungstic acid (HSiW) catalyst under mild conditions in air to afford addition products in good to excellent yields.

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.

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.

Zirconium-catalyzed intermolecular hydroamination of unactivated olefins

Highly efficient hydroamination reactions of sulfonamides, carboxamides, and carbamates with unactivated olefins catalyzed by simple and inexpensive zirconium salts under mild reaction conditions were presented for the practical preparation of various amines. These processes gave good to excellent yields of the addition products in Markovnikov addition fashion. Georg Thieme Verlag Stuttgart.

Copper-Catalyzed C(sp3)?H Amidation: Sterically Driven Primary and Secondary C?H Site-Selectivity

Undirected C(sp3)?H functionalization reactions often follow site-selectivity patterns that mirror the corresponding C?H bond dissociation energies (BDEs). This often results in the functionalization of weaker tertiary C?H bonds in the presence of stronger secondary and primary bonds. An important, contemporary challenge is the development of catalyst systems capable of selectively functionalizing stronger primary and secondary C?H bonds over tertiary and benzylic C?H sites. Herein, we report a Cu catalyst that exhibits a high degree of primary and secondary over tertiary C?H bond selectivity in the amidation of linear and cyclic hydrocarbons with aroyl azides ArC(O)N3. Mechanistic and DFT studies indicate that C?H amidation involves H-atom abstraction from R-H substrates by nitrene intermediates [Cu](κ2-N,O-NC(O)Ar) to provide carbon-based radicals R. and copper(II)amide intermediates [CuII]-NHC(O)Ar that subsequently capture radicals R. to form products R-NHC(O)Ar. These studies reveal important catalyst features required to achieve primary and secondary C?H amidation selectivity in the absence of directing groups.

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

Mechanistic studies of the hydroamination of norbornene with electrophilic platinum complexes: The role of proton transfer

Hydroaminations of norbornene with arylsulfonamides and weakly basic anilines were achieved using electrophilic Pt(II) bis(triflate) complexes of the type L2Pt(OTf)2 (L2 = tBu 2bpy, tBuC6H4N= C(CH 3)C(CH3)=NC6H4tBu, (C6H5)2PCH2CH2P(C 6H5)2, (C6F5) 2PCH2CH2P(C6F5) 2, S-BINAP). Pseudo-first-order kinetics reveal little to no dependence of the reaction rate on the ancillary ligand. Mechanistic studies do not favor an olefin coordination mechanism but are instead consistent with a mechanism involving sulfonamide coordination and generation of an acidic proton that is transferred to the norbornene. It is postulated that the resulting norbornyl cation is then attacked by free sulfonamide, and loss of proton from this adduct completes the hydroamination. The platinum-sulfonamide complex readily undergoes deprotonation to give μ-amido platinum-bridged dimer that was isolated from the reaction solution. These studies also involve use of Me3SiPh and Me3SnPh as non-nucleophilic proton traps. Cleavage of the Ph-E bonds was used to detect the acidic, catalytically active species.

Radical transfer hydroamination with aminated cyclohexadienes using polarity reversal catalysis: Scope and limitations

The synthesis of various new 1-aminated-2,5-cyclohexadienes is described. These reagents can be used in radical transfer hydroaminations of unactivated and electron-rich double bonds. With thiols as polarity reversal catalysts good yields are obtained. The radical hydroamination occurs with good to excellent anti-Markovnikov selectivity. Many functional groups such as alcohols, silyl ethers, phosphonates, arylbromides, imides, amides, and also acidic protons are tolerated under the reaction conditions. DFT calculations provide insights into the aromatization of silyl, alkyl, and aminyl substituted cyclohexadienyl radicals to generate the corresponding C-, Si-, and N-centered radicals.

Mechanistic studies of the copper-catalyzed electrophilic amination of diorganozinc reagents and development of a zinc-free protocol

Equation Presented An SN2 mechanism for the copper-catalyzed amination of diorganozinc reagents by O-benzoyl-N,N-dialkylhydroxyamines is supported by following stereochemically defined organometallics through the reaction and by employing the endocyclic restriction test. A copper-catalyzed electrophilic amination of organomagnesium compounds is also described in which the use of zinc halides has been eliminated.

MICROBIAL TRANSFORMATIONS. PART 7 (1) BIOHYDROXYLATION OF BORNYLAMIDE DERIVATIVES BY THE FUNGUS BEAUVERIA SULFURESCENS

The biohydroxylation of various amide derivatives of norbornane and of camphane have been studied, in order to explore the possible influence of this amide group configuration and substitution upon the regio, the stereo and the enantioselectivity of the p