5614-35-7

Upstream product

• 1521-51-3 rac-3-bromocyclohexene 
• 108-95-2 phenol 
• 2441-97-6 3-chloro-cyclohexene 
• 822-67-3 Cyclohex-2-enol 
• 108-98-5 thiophenol 
• 122-79-2 Phenyl acetate 
• 110-83-8 cyclohexene 
• 98-80-6 phenylboronic acid 
• 1165952-91-9 cyclohexa-1,3-diene 
• 7429-37-0 trans-1,2-dibromocyclohexane 
• 139-02-6 sodium phenoxide 
• 64-17-5 ethanol 
• 201230-82-2 carbon monoxide 
• 119825-50-2 1-(ethoxycarbonyloxy)-2-cyclohexene 

Downstream Products

• 1200250-04-9 N-2-cyclohexenyl-N-methyl-1-naphthylmethylamine 
• 13524-72-6 1-(2-hydroxyphenyl)cyclohexene 
• 13524-79-3 1,2,3,4,4a,9b-hexahydrodibenzo[b,d]furan 
• 108-95-2 phenol 
• 97418-47-8 2-phenoxy-adipic acid 
• 14003-77-1 3-(2-hydroxyphenyl)cyclohexene 
• 13130-19-3 1,2,3,4-tetrahydrodibenzo[b,d]furan 
• 27124-70-5 1-(cyclohex-2-enyl)-2-methoxybenzene 
• 59457-19-1 (2-cyclohex-2-enyl-phenoxy)-acetic acid 
• 108661-67-2 (1R,2S,6R)-2-Morpholin-4-yl-6-phenoxy-cyclohexanol 
• 108661-68-3 1-((1R,2S,3S)-2-Hydroxy-3-phenoxy-cyclohexyl)-4-phenyl-piperidin-4-ol 

Relevant academic research and scientific papers

URJC-1-MOF as New Heterogeneous Recyclable Catalyst for C-Heteroatom Coupling Reactions

Guillermo Calleja and co-workers from @urjc describe URJC-1-MOF as a new heterogeneous recyclable catalyst for c-heteroatom coupling reactions. The capacity of copper-based URJC-1-MOF as a MOF catalyst in cross-coupling reactions has been evaluated, focusing on the Chan-Lam-Evans arylation-type reactions on amines and alcohols without extra additives or ligands. The extraordinary chemical and structural stability of URJC-1-MOF and its good specific surface, make this material a promising alternative to homogeneous Cu (II) catalysts for cross-coupling reactions. URJC-1-MOF showed a remarkable catalytic activity for cross-coupling C?N and C?O reactions, higher than other heterogeneous and homogeneous copper-based catalyst, such as CuO, HKUST-1, Cu?MOF-74, Cu(OAc)2 and CuSO4?5H2O. Moreover, its easy recovery by simple filtration and reusability in successive runs without any loss of activity and stability, demonstrates the potential of URJC-1-MOF as an alternative catalyst for this kind of reactions in different chemical media of industrial interest.

Rearrangements of Cycloalkenyl Aryl Ethers

Rearrangement reactions of cycloalkenyl phenol and naphthyl ethers and the acid-catalyzed cyclization of the resulting product were investigated. Claisen rearrangement afforded 2-substituted phenol and naphthol derivatives. Combined Claisen and Cope rearrangement resulted in the formation of 4-substituted phenol and naphthol derivatives. In the case of cycloocthylphenyl ether the consecutive Claisen and Cope rearrangements were followed by an alkyl migration. The mechanism of this novel rearrangement reaction is also discussed.

Copper Catalyzed sp3 C-H Etherification with Acyl Protected Phenols

A variety of acyl protected phenols AcOAr participate in sp3 C-H etherification of substrates R-H to give alkyl aryl ethers R-OAr employing tBuOOtBu as oxidant with copper(I) β-diketiminato catalysts [CuI]. Although 1°, 2°, and 3° C-H bonds may be functionalized, selectivity studies reveal a preference for the construction of hindered, 3° C-OAr bonds. Mechanistic studies indicate that β-diketiminato copper(II) phenolates [CuII]-OAr play a key role in this C-O bond forming reaction, formed via transesterification of AcOAr with [CuII]-OtBu intermediates generated upon reaction of [CuI] with tBuOOtBu.

Gold catalysis: Experimental mechanistic insights into the anellation of phenols with 1,3-dienes Dedicated to Prof. Hubert Schmidbaur on the occasion of his 80th birthday.

An intermediate of the anellation reaction of phenols and 1,3-dienes could be detected, isolated and characterized as the hydroarylation product. The other conceivable intermediate, the hydroaryloxylation product, was prepared via Pd-catalysis and converted under the conditions of the gold catalysis, too. Under exactly the same conditions a very fast Claisen rearrangement took place delivering the formal hydroarylation product as well. After this fast intermolecular formation of the intermediate (formed either directly via the hydroarylation pathway or via a hydroaryloxylation/Claisen rearrangement sequence) the subsequent intramolecular reaction leading to the product turned out to be significantly slower. The major product is the cis-diastereomer (cis-3/trans-3 = 12:1).

CATALYTIC C-H BOND ACTIVATION FOR THE SYNTHESIS OF ETHERS AND THIOETHERS

Disclosed is a method for the transition metal-mediated oxidation of C-H bonds to form C-0 or C-S bonds. The methods are useful for the formation of ethers (R-OR') from alcohols, R'OH, and sp3 -hybridized C-H bonds in substrates, R-H. Aryl or heteroaryl acetates may also be used for C-H to C-OAr bond formation. The methods are also useful in the preparation of C-S bonds from acetyl-protected thiols, MeC(0)SR, and disulfides, RSSR. Advantageously, the methods minimize reaction steps, the handling of oxidized intermediates, and environmental impact.

Lanthanide complexes in organic synthesis: Synthesis of ethers from allyl alcohols

Coordinatively unsaturated lanthanide ions catalyze a wide variety of organic reactions. The hepta coordinated Ln(III) complexes with N,N′-ethylene-bis-(2-aminobenzamide) [EBAB] and N,N′ -propylene-bis-(2-aminobenzamide) [PBAB], the [Ln(EBAB)Cl3/sub

Palladium-Catalyzed Equilibrium Addition of Acidic OH Groups across Dienes

Mildly acidic O-H groups undergo transition-metal-catalyzed reversible addition across the C=C bonds of cyclic and acyclic dienes. For example, the simple complex [Pd(PPh3)4] (1 mol%) effectively catalyzes both the forward addition o

Molybdenum(II)-catalyzed allylation of electron-rich aromatics and heteroaromatics

The stable, readily available molybdenum(II) complexes [Mo(CO)4Br2]2 (B) and Mo(CO)3(MeCN)2-(SnCl3)Cl (C) have been found to catalyze C-C bond- forming allylic substitution with electronrich aromatics (e.g., 15 + PhOMe → 62) and heteroaromatics (e.g., 15 + 36 → 88) as nucleophiles under mild conditions (room temperature, 30 min-3 h). Remarkable is the para-selectivity for anisole, whereas phenol tends to favor ortho-substitution in certain instances. Mechanistic and stereochemical experiments are indicative of Lewis-acid catalysis rather than a metal template-controlled process.

Palladium( 0) -catalyzed phenoxycarbonylation of allylic carbonates

Phenoxycarbonylation of various allylic carbonates under various conditions in tetrahydrofuran is described. The nature and ratio of the products formed are dependent on the presence of water, carbon monoxide pressure and addition of various inorganic halides. The formation of a product arising from dimerization of the allylic carbonate is discussed.