20743-91-3

Upstream product

• 544-10-5 1-Chlorohexane 
• 150-76-5 4-methoxy-phenol 
• 696-62-8 para-iodoanisole 
• 111-27-3 hexan-1-ol 
• 92149-07-0 4,7-dimethoxy-1,10-phenanthroline 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 122004-89-1 6-(4-methoxyphenoxy)hexan-1-ol 
• 4286-55-9 1-bromo-6-hexanol 
• 1383151-90-3 C₁₃H₁₈O₃ 
• 111-25-1 1-bromo-hexane 

Downstream Products

• 1265919-64-9 1-hexyloxy-4-methoxy-3-nitrobenzene 
• 1265919-63-8 1-hexyloxy-4-methoxy-2,5-dinitrobenzene 
• 218141-98-1 1,4-bis(chloromethyl)-2-hexyloxy-5-methoxybenzene 

Relevant academic research and scientific papers

Copper-catalyzed hydroxylation of aryl halides: Efficient synthesis of phenols, alkyl aryl ethers and benzofuran derivatives in neat water

A thorough study of environmentally friendly hydroxylation of aryl halides is presented. The best protocol consists of hydroxylation of different aryl bromides and electron-deficient aryl chlorides by water solution of tetrabutylammonium hydroxide catalyzed by Cu2O/4,7-dihydroxy-1,10-phenanthroline. Various phenol derivatives can be obtained in excellent selectivity and great functional group tolerance. This methodology also provides a direct pathway for the formation of alkyl aryl ethers and benzofuran derivatives in a one-pot tandem reaction.

Chemoselective, Scalable Nickel-Electrocatalytic O-Arylation of Alcohols

The formation of aryl-alkyl ether bonds through cross coupling of alcohols with aryl halides represents a useful strategic departure from classical SN2 methods. Numerous tactics relying on Pd-, Cu-, and Ni-based catalytic systems have emerged over the past several years. Herein we disclose a Ni-catalyzed electrochemically driven protocol to achieve this useful transformation with a broad substrate scope in an operationally simple way. This electrochemical method does not require strong base, exogenous expensive transition metal catalysts (e.g., Ir, Ru), and can easily be scaled up in either a batch or flow setting. Interestingly, e-etherification exhibits an enhanced substrate scope over the mechanistically related photochemical variant as it tolerates tertiary amine functional groups in the alcohol nucleophile.

Unprecedented Regioregular Poly(1,4-arylene)s Prepared by Nickel(II)-Catalyzed Cross-Coupling Polymerization of 2,5-Disubstituted Bromo(chloro)arylene

The unprecedented synthesis of regioregular head-to-tail-type poly(1,4-arylene)s bearing different substituents at the 2- and 5-positions is described. They were prepared by the polymerization of 2,5-disubstituted bromo(chloro)arylenes by selective halogen–metal exchange with a Grignard reagent and subsequent cross-coupling polymerization with a nickel catalyst [NiCl2(dppp)]. Formation of the regioregular poly(1,4-arylene)s were confirmed by NMR spectroscopy, and showed remarkable differences to those polymers having uncontrolled regioregularity. Polymerization of bromo(chloro)arylenes with a chiral alkoxy substituent also led to the regioregular head-to-tail-type polyarylene, which demonstrated circular dichroism, thus suggesting formation of a structure with higher-order regularity.

Chemoselective deoxygenation of ether-substituted alcohols and carbonyl compounds by B(C6F5)3-catalyzed reduction with (HMe2SiCH2)2

B(C6F5)3-catalyzed deoxygenation of ether-substituted alcohols and carbonyl compounds has been developed using (HMe2SiCH2)2 as the reductant. This unique reagent shows distinct superiority over traditional one silicon-centered hydrosilanes, giving the corresponding alkanes in high yields with good tolerance of ethers, aryl halides and alkenes. The control experiments suggest that (HMe2SiCH2)2 might facilitate the approach in an intramolecular Si/O activation manner.

Copper and l-sodium ascorbate catalyzed hydroxylation and aryloxylation of aryl halides

CuSO4·5H2O and NaAsc catalyzed hydroxylation and C-O/C-S cross-coupling reactions of aryl halides with phenols or 4-methylbenzenethiol were described. A wide range of substrates and test cases highlight the synthetic utility of the approach. A series of phenols, diaryl ethers, alkylaryl ethers, and diaryl thioethers were synthesized in high yield.

Selective catalytic synthesis of unsymmetrical ethers from the dehydrative etherification of two different alcohols

The cationic ruthenium-hydride complex [(C6H6)(PCy3)(CO)RuH]+BF4- catalyzes selective etherification of two different alcohols to form unsymmetrically substituted ethers. The catalytic method exhibits a broad substrate scope while tolerating a range of heteroatom functional groups in forming unsymmetrical ethers, and it is successfully used to directly synthesize a number of highly functionalized chiral nonracemic ethers.

Alkoxylation reactions of aryl halides catalyzed by magnetic copper ferrite

Copper ferrite (CuFe2O4), which is easy-made, air-stable, low cost, easy separable, and regenerable, was applied as catalyst in an efficient method for C-O coupling reactions between various kinds of unactivated alkyl alcohols and aryl halides. This method only adopts 2.5% mol CuFe2O4 catalyst and selectively proceeds to C-O bond formation even sensitive substituents exist in the system.

An improved Cu-based catalyst system for the reactions of alcohols with aryl halides

(Chemical Equation Presented) The use of 3,4,7,8-tetramethyl-1,10- phenanthroline (Me4Phen) as a ligand improves the Cu-catalyzed cross-coupling reactions of aryl iodides and bromides with primary and secondary aliphatic, benzylic, allylic, and propargylic alcohols. Most importantly, by employing this catalyst system, the need to use an excessive quantity of the alcohol coupling partner is alleviated. The relatively mild conditions, short reaction times, and moderately low catalyst loading allow for a wide array of functional groups to be tolerated on both the electrophilic and nucleophilic coupling partners.

Organosoluble copper clusters as precatalysts for carbon - Heteroelement bond-forming reactions: Microwave and conventional heating

(Chemical Equation Presented). The coupling of aryl iodides with alcohols under mild conditions has been explored using self-assembled octanuclear copper clusters as catalysts. Reactions involving tetrahydrofurfuryl alcohol were typically complete in 4-8

Photo-oxidation phenomenon of MH-PPV films studied by ellipsometry and infrared spectroscopy

In this paper we study the photo-oxidation phenomenon in the structure of a PPV derivative, the poly[(2-methoxy-5-hexyloxy)-p-phenylenevinylene] - (MH-PPV), using ellipsometry and infrared spectroscopy techniques. Ellipsometric measurements were carried o