7325-14-6

Upstream product

• 108-93-0 cyclohexanol 
• 71-43-2 benzene 
• 7446-70-0 aluminium trichloride 
• 110-83-8 cyclohexene 
• 7664-93-9 sulfuric acid 
• 542-18-7 cyclohexyl chloride 
• 827-52-1 1-phenyl-1-cyclohexane 
• 626-39-1 1,3,5-trisbromobenzene 
• 256390-55-3 cyclohexylzinc chloride 
• 931-48-6 2-cyclohexylacetylene 
• 108-85-0 1-bromocyclohexane 
• 97084-94-1 1,2,4,5-tetracyclohexylbenzene 
• 538-75-0 dicyclohexyl-carbodiimide 
• 1087-02-1 1,4-dicyclohexyl-benzene 

Downstream Products

• 97443-80-6 (2-bromobenzene-1,3,5-triyl)tricyclohexane 
• 612-71-5 1,3,5-triphenylbenzene 
• 554-95-0 benzene-1,3,5-tricarboxylic acid 
• 6297-08-1 1,3,5-tricyclohexyl-cyclohexane 
• 1234866-58-0 2,4,6-tricyclohexylbenzenesulfonyl chloride 
• 1309446-13-6 (R_a)-3,3’-bis(2,4,6-tricyclohexylphenyl)-[1,1’-binaphthalene]-2,2’-diol 
• 40049-67-0 1-nitro-2,4,6-tricyclohexylbenzene 
• 820217-06-9 (2,4,6-tricyclohexylphenyl)magnesium bromide 
• 1309446-13-6 (S)-3,3'-bis-(2,4,6-tricyclohexylphenyl)-[1,1']-binaphthalenyl-2,2'-diol 
• 119530-83-5 (+/-)-phthalic acid mono-[1-(2,4,6-tricyclohexyl-phenyl)-ethyl ester] 
• 119530-83-5 phthalic acid mono-[(R)-1-(2,4,6-tricyclohexyl-phenyl)-ethyl ester] 

Relevant academic research and scientific papers

An Alternative Synthesis of Cycloalkyl-Substituted CPA Catalysts and Application in Asymmetric Protonation Reactions**

An alternative synthesis of cycloalkyl-substituted CPA catalysts is reported. A Negishi coupling offers improved yields and purity of the necessary 1,3,5-tri(cycloalkyl)benzenes. Limitations in the use of commercial organozinc reagents have been identifie

Iron-catalyzed trimerization of terminal alkynes enabled by pyrimidinediimine ligands: A regioselective method for the synthesis of 1,3,5-substituted arenes

The development of pyrimidine-based analogues of the well-known pyridinediimine (PDI) iron complexes enables access to a functional-group-tolerant methodology for the catalytic trimerization of terminal aliphatic alkynes. Remarkably, in contrast to established alkyne trimerization protocols, the 1,3,5-substituted arenes are the main reaction products. Preliminary mechanistic investigations suggest that the enhanced π-acidity of the pyrimidine ring, combined with the hemilability of the imine groups coordinated to the iron center, facilitates this transformation. The entry point in the catalytic cycle is an isolable iron dinitrogen complex. The catalytic reaction proceeds via a 1,3-substituted metallacycle, which explains the observed 1,3,5-regioselectivity. Such a metallacycle could be isolated and represents a rare 1,3-substituted ferracycle obtained through alkyne cycloaddition.

H-BPin/KOtBu Promoted Activation of Cobalt Salt to a Heterotopic Catalyst for Highly Selective Cyclotrimerization of Alkynes

A mixture of HBPin with KOtBu was found to activate cobalt salt to form a heterotopic cobalt species that is highly active for catalytic intermolecular trimerization of alkynes. This protocol affords 1,2,4-regioisomers in good yields with high regioselectivities under mild conditions. These salient features, together with the operational simplicity and high efficiency, as well as obviating the use of any costly and/or air sensitive ligands, renders the protocol promising for practical applications.

Combined Photoredox and Iron Catalysis for the Cyclotrimerization of Alkynes

Successful combinations of visible-light photocatalysis with metal catalysis have recently enabled the development of hitherto unknown chemical reactions. Dual mechanisms from merging metal-free photocatalysts and earth-abundant metal catalysts are still in their infancy. We report a photo-organo-iron-catalyzed cyclotrimerization of alkynes by photoredox activation of a ligand-free Fe catalyst. The reaction operates under very mild conditions (visible light, 20 °C, 1 h) with 1–2 mol percent loading of the three catalysts (dye, amine, FeCl2).

From alkylarenes to anilines via site-directed carbon–carbon amination

Anilines are fundamental motifs in various chemical contexts, and are widely used in the industrial production of fine chemicals, polymers, agrochemicals and pharmaceuticals. A recent development for the synthesis of anilines uses the primary amination of C–H bonds in electron-rich arenes. However, there are limitations to this strategy: the amination of electron-deficient arenes remains a challenging task and the amination of electron-rich arenes has a limited control over regioselectivity—the formation of meta-aminated products is especially difficult. Here we report a site-directed C–C bond primary amination of simple and readily available alkylarenes or benzyl alcohols for the direct and efficient preparation of anilines. This chemistry involves a novel C–C bond transformation and offers a versatile protocol for the synthesis of substituted anilines. The use of O2 as an environmentally benign oxidant is demonstrated, and studies on model compounds suggest that this method may also be used for the depolymerization of lignin.

Aromatic amine compound synthesis method

The invention discloses an aromatic amine compound synthesis method which is characterized in that the method is implemented according to any of two methods. The first method includes the steps: mixing an alkyl aromatic compound with a general formula (I) and a nitrogen-containing compound with a general formula (II); performing reaction on mixture under an oxidizing agent and an organic solvent to obtain an aromatic amine compound with a general formula (III). The second method includes the steps: mixing an aromatic alcohol derivative with a general formula (I') and the nitrogen-containing compound with the general formula (II); performing reaction on mixture under an acid additive and an organic solvent to prepare the aromatic amine compound with the general formula (III). According to the method, a lot of alkyl aromatic compounds or aromatic alcohol derivatives firstly serve as raw materials, and the raw materials are reacted to generate the aromatic amine compound without the action of metal catalysis. Compared with a traditional synthesis method, the synthesis method has the advantages that the method is high in yield and simple in condition, waste discharging amount is less,metal participation is omitted, a reaction device is simple, industrial production is easily achieved and the like. The method has a wide application prospect.

Organocatalytic Kinetic Resolution of Sulfoximines

An efficient kinetic resolution of sulfoximines with enals was realized using chiral N-heterocyclic carbene (NHC) catalysts. The stereoselective amidation proceeds without additional acyl transfer agent. Both enantiomers of the sulfoximines can be obtaine

Silica-supported tungsten carbynes (≡SiO)xW(≡CH)(Me)y (x = 1, y = 2; X = 2, y = 1): New efficient catalysts for alkyne cyclotrimerization

The activity of silica-supported tungsten carbyne complexes (≡SiO)xW(≡CH)(Me)y (x = 1, y = 2; x = 2, y = 1) toward alkynes is reported. We found that they are efficient precatalysts for terminal alkyne cyclotrimerization with high TONs. We also demonstrate that this catalyst species is active for alkyne cyclotrimerization without the formation of significant alkyne metathesis products. Additional DFT calculations highlight the importance of the W coordination sphere in supporting this experimental behavior.

Enantioselective halogenative semi-pinacol rearrangement: Extension of substrate scope and mechanistic investigations

The present Full Paper article discloses a survey of our recent results obtained in the context of the enantioselective halogenation-initiated semi-pinacol rearrangement. Commencing with the fluorination/semi-pinacol reaction first and moving to the heavier halogens (bromine and iodine) second, the scope and limitations of the halogenative phase-transfer methodology will be discussed and compared. An extension of the fluorination/semi-pinacol reaction to the ring-expansion of five-membered allylic cyclopentanols will be also described, as well as some preliminary results on substrates prone to desymmetrization will be given. Finally, the present manuscript will culminate with a detailed mechanistic investigation of the canonical fluorination/semi-pinacol reaction. Our mechanistic discussion will be based on in situ reaction progress monitoring, complemented with substituent effect, kinetic isotopic effect and non-linear behaviour studies.

Metal complexes of very bulky N,N′-diarylimidazolylidene N-heterocyclic carbene (NHC) ligands with 2,4,6-cycloalkyl substituents

1,3,5-Tricycloalkylbenzene (cycloalkyl = C5H9, C6H11) was converted into the respective anilines (by means of nitration and reduction) and then into the corresponding diimines (with glyoxal), the cyclization of