52034-22-7

Upstream product

• 822-67-3 Cyclohex-2-enol 
• 62-53-3 aniline 
• 2441-97-6 3-chloro-cyclohexene 
• 622-37-7 Phenyl azide 
• 110-83-8 cyclohexene 
• 98-95-3 nitrobenzene 
• 1165952-91-9 cyclohexa-1,3-diene 
• 100-65-2 N-Phenylhydroxylamine 
• 68234-27-5 1′,2′,3′,6′-tetrahydro-[1,1′-biphenyl]-2-amine 
• 95-51-2 o-chloroaniline 
• 1521-51-3 rac-3-bromocyclohexene 
• 15717-36-9 1-(cyclohex-2-enyl)-1,3-diphenylurea 
• 106-38-7 para-bromotoluene 
• 84487-67-2 N-(Δ²-cyclohexenyl)-o-chloroaniline 

Downstream Products

• 59816-86-3 1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-amine 
• 62-53-3 aniline 
• 226216-99-5 N-(cyclohex-2-enyl)-N-phenyl-2-bromopropanamide 
• 226216-98-4 N-(2-cyclohexenyl)-N-phenylbromoacetamide 
• 32720-57-3 4-(cyclohex-2-en-1-yl)morpholine 
• 10592-26-4 N-(1-Cyclohexen-1-yl)benzolamin 
• 15717-36-9 1-(cyclohex-2-enyl)-1,3-diphenylurea 
• 58981-52-5 3-methyl-1-phenyl-1,3,3a,6,7,7a-hexahydro-indol-2-one 
• 1421845-66-0 C₁₅H₁₅NO 
• 1421845-48-8 C₁₅H₁₅NO 

Relevant academic research and scientific papers

Silver Salt-Mediated Allylation Reactions Using Allyl Bromides

A facile, efficient, and chemoselective synthesis of allylic amides has been developed. Allyl bromides were used as the precursors activated by silver triflate. A Ritter-type reaction readily proceeded to give various allyl amides under mild conditions. The reaction protocol was also applicable to different nucleophilic partners to give a wide range of allyl-substituted products in the absence of a base.

Metal-organic frameworks containing nitrogen-donor ligands for efficient catalytic organic transformations

Metal-organic framework (MOFs) compositions based on nitrogen donor-based organic bridging ligands, including ligands based on 1,3-diketimine (NacNac), bipyridines and salicylaldimine, were synthesized and then post-synthetically metalated with metal precursors, such as complexes of first row transition metals. Metal complexes of the organic bridging ligands could also be directly incorporated into the MOFs. The MOFs provide a versatile family of recyclable and reusable single-site solid catalysts for catalyzing a variety of asymmetric organic transformations. The solid catalysts can also be integrated into a flow reactor or a supercritical fluid reactor.

A lutidine-promoted photoredox catalytic atom-transfer radical cyclization reaction for the synthesis of 4-bromo-3,3-dialkyl-octahydro-indol-2-ones

Reported herein is a visible-light-catalyzed photoredox atom-transfer radical cyclization (ATRC) halo-alkylation of 1,6-dienes with α-halo-ketones as the ATRC reagent. This process exhibits high atom economy, high step economy, and high redox economy, which can directly construct a 4-bromo-3,3-dialkyl-octahydro-indol-2-one core under mild conditions in one pot, and lutidine is found to be the key promoter for this ATRC process.

Method for preparing allylamine compounds

The invention discloses a method for preparing allylamine compounds. The allylamine compounds are synthesized by taking an ionic iron (III) complex which has a molecular formula of [(RNCH2CH2NR)CH][FeBr4] (R is tert-butyl) and contains 1,3-di-tert-butyl imidazoline cation as a catalyst, taking di-tert-butyl peroxide as an oxidant and carrying out oxidative coupling reaction on amine compounds andallyl hydrocarbon compounds. The method disclosed by the invention has wide application range, can be used for aromatic amine containing an electron-withdrawing group, is effective for aromatic aminecontaining an electron-donating group, and is a first case of preparing the allylamine compounds through the oxidative coupling reaction of the amine compounds and the allyl hydrocarbon compounds, which is realized by an iron-based catalyst.

Oxidative amination of benzylic alkanes with nitrobenzene derivatives as nitrogen sources

The oxidative amination of inert C[sbnd]H bonds has the potential to fundamentally change chemistry but is severely limited by the low chemo- and regio-selectivity under oxidation conditions. Until now, no efficient methodology for the direct intermolecular amination of terminal sp3-C[sbnd]H bonds to N-alkyl amines has existed. Here, a new concept is proposed for the oxidative amination of the terminal sp3-C[sbnd]H bond in alkanes via the construction of a complex reaction system composed of a carbon-supported Co-Ni bimetallic catalyst, an alkane, nitrobenzene, tert-butyl hydroperoxide and hydrogen. This system allows the reduction of nitrobenzene to aniline and the further oxidative amination of the alkane. Nitrobenzene and toluene derivatives can be successfully transformed into the corresponding N-benzyl aniline derivatives with up to 95% isolated yields, and the reaction shows excellent functional group tolerance. This approach offers a new concept for catalyst design and may strongly promote the study of inert C[sbnd]H bond activation and the synthesis of functional N-containing compounds.

Copper-Catalyzed Intramolecular Oxidative Amination of Unactivated Internal Alkenes

A copper-catalyzed oxidative amination of unactivated internal alkenes has been developed. The Wacker-type oxidative alkene amination reaction is traditionally catalyzed by a palladium through a mechanism involving aminopalladation and β-hydride elimination. Replacing the precious and scarce palladium with a cheap and abundant copper for this transformation has been challenging because of the difficulty associated with the aminocupration of internal alkenes. The combination of a simple copper salt, without additional ligand, as the catalyst and Dess-Martin periodinane as the oxidant, promotes efficiently the oxidative amination of allylic carbamates and ureas bearing di- and trisubstituted alkenes leading to oxazolidinones and imidazolidinones. Preliminary mechanistic studies suggested a hybrid radical-organometallic mechanism involving an amidyl radical cyclization to form the key C-N bond.

BIS(PHOSPHINE)-CARBODICARBENE CATALYST COMPLEXES AND METHODS OF USING THE SAME

An organometallic complex of a tridentate bis(phosphine)-carbodicarbene ligand and a transition metal, is described. In some embodiments the ligand has the structure of Formula (I): The complexes are useful in methods of making an allylic amine carried ou

Intermolecular hydroamination of 1,3-dienes catalyzed by bis(phosphine)carbodicarbene-rhodium complexes

A carbodicarbene (CDC)-based pincer ligand scaffold is reported, along with its application to site-selective Rh(I)-catalyzed intermolecular hydroamination of 1,3-dienes with aryl and alkyl amines. To the best of our knowledge, this is the first example of the use of a well-defined CDC complex as an efficient catalyst. Transformations proceed in the presence of 1.0-5.0 mol % Rh complex at 35-120 °C; allylic amines are obtained in up to 97% yield and with >98:2 site selectivity.

N-Bu4NI/TBHP-catalyzed direct amination of allylic and benzylic C(sp3)-H with anilines under metal-free conditions

A novel and efficient n-Bu4NI/TBHP-catalyzed direct amination of allylic and benzylic C(sp3)-H with anilines to form N-substituted anilines under metal-free conditions has been developed. the Partner Organisations 2014.

Hydrogen-bond-assisted activation of allylic alcohols for palladium-catalyzed coupling reactions

We report direct activation of allylic alcohols using a hydrogen-bond-assisted palladium catalyst and use this for alkylation and amination reactions. The novel catalyst comprises a palladium complex based on a functionalized monodentate phosphoramidite ligand in combination with urea additives and affords linear alkylated and aminated allylic products selectively. Detailed kinetic analysis show that oxidative addition of the allyl alcohol is the rate-determining step, which is facilitated by hydrogen bonds between the alcohol, the ligand functional group, and the additional urea additive. Hydrogen Bond Rule(s): Direct activation of allylic alcohols and subsequent alkylation and amination reactions are reported. The new catalyst is based on functionalized palladium and phosphoramidite ligands to allow hydrogen bond-assisted activation. Kinetic data are in line with this mechanism as the oxidative addition is the rate-determining step.