- Diaryl Ether Formation Merging Photoredox and Nickel Catalysis
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Photoredox and Ni catalysis are combined to produce diaryl ethers under mild conditions. A broad range of aryl halides and phenol derivatives are cross-coupled in the presence of a readily available organic photocatalyst and NiBr2(dtbpy). Symmetrical diaryl ethers have also been directly obtained from aryl bromides in the presence of water. Mechanistic investigations support the involvement of Ni(0) species at the outset of the reaction and a Ni(II)/Ni(III)-photocatalyzed single electron transfer process preceding the productive C(sp2)-OAr reductive elimination.
- Liu, Le,Nevado, Cristina
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supporting information
p. 2188 - 2193
(2021/05/04)
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- Acid-catalyzed synthesis of condensed polycyclic diaryl ethers from arenols
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Diaryl ethers containing condensed polycyclic aryl groups were synthesized from arenols in the presence of a catalytic amount of p-chlorobenzenesulfonic acid. Symmetrical binaphthyl, biphenanthryl, and bipyrenyl ethers were obtained in high yields. Unsymmetrical derivatives were also synthesized from 9-phenanthrol and arenols, using combinations of reactive and unreactive substrates.
- Tanii, Saori,Arisawa, Mieko,Yamaguchi, Masahiko
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supporting information
p. 14078 - 14080
(2019/11/25)
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- Method for synthesizing 2,2'-dinaphthyl ether
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The application relates to a method for synthesizing 2,2'-dinaphthyl ether. The method comprises the following specific steps: taking 2-naphthol and 2-bromonaphthalene as raw materials, adopting monovalent metal oxide and a diamine ligand as a catalyst system, and synthesizing to obtain the 2,2'-dinaphthyl ether by using an Ullmann diaryl ether synthesis method; then respectively adopting a separate purification scheme to avoid the use of chromatography. Products with the purity of 99 percent are obtained at the yield of nearly 70 percent, so the method has high industrial application value.
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Paragraph 0033-0038; 0040-0042
(2018/07/06)
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- Base-mediated N- And O-arylations of NH-containing heterocycles, heterocyclic amines and phenols
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Nucleophilic substitution reactions of N-heterocycles such as imidazole, benzimidazole, indole and pyrazole as well as NH2 or OH containing heterocycles, with electron-deficient aryl halides in the presence of t-BuOK or K2CO3as base and DMSO as solvent are reported. A series of N-aryl azoles, unsymmetric diaryl ethers and diaryl amines were obtained in good yields.
- Ghasemi, Zarrin,Shahrak, Nasim Shahi,Roomi, Behzad Jalali,Zakeri, Ziba
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- Bismuth(III)-catalyzed dehydrative etherification and thioetherification of phenolic hydroxy groups
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Use of a bismuth catalyst allowed efficient dehydrative substitution of phenolic hydroxy groups with alcohols and thiols to form C-O and C-S bonds. The reaction required equimolar amounts of two readily available substrates that generated H2O as the only byproduct. The relatively mild reaction conditions were compatible with the functional groups selected, and provided excellent chemoselectivity.
- Murai, Masahito,Origuchi, Kazuki,Takai, Kazuhiko
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supporting information
p. 3828 - 3831
(2014/08/05)
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- Synthesis of chromans via [3 + 3] cyclocoupling of phenols with allylic alcohols using a Mo/o-chloranil catalyst system
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(Chemical Equation Presented) The combination of a molybdenum complex (CpMoCl(CO)3 or [CpMo(CO)3]2) and o-chloranil was used as a catalyst in the [3 + 3] cyclocoupling of phenols and allylic alcohols under microwave heating conditions. Substituted chromans were selectively obtained in moderate to good isolated yields.
- Yamamoto, Yoshihiko,Itonaga, Kouhei
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scheme or table
p. 717 - 720
(2009/08/19)
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- Compositions containing esters of aromatic alkoxylated alcohols and fatty carboxylic acids
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A personal care or cosmetic product composition that includes from about 0.1% to about 99% of at least one ester of alkoxylated aromatic alcohol and fatty carboxylic acid, and from about 0.1% to 60% of at least one functional ingredient is provided. The functional ingredients in the composition may include active ingredients and additional ingredients. Especially suitable active ingredients are sunscreen active ingredients and antiperspirant active ingredients. Preferred compositions are sunscreen product formulations and antiperspirant products. In one preferred embodiment, the composition further includes at least one cyclomethicone compound present in the amount of from about 1% to 99% by weight of the composition. A method of improving the protection of human or animal skin or hair from radiation and a method of improving the protection of human or animal skin or hair from perspiration are also provided.
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- Thiones as reactive intermediates in condensations of diketones with aromatics mediated by tetraphosphorus decasulfide
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Phenanthrene-9,10-quinone and P4S10 react with phenols on being heated to give oxathiins, e.g., 9 the dioxin 22, ethers, e.g., 14 arylphenanthrenols, e.g., 10 and furanols, e.g., 17 in addition to sulfides, e.g., 26 and disulfides, e
- Morrison, Brian J.,Musgrave, Oliver C.
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p. 2725 - 2744
(2007/10/03)
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- A highly selective synthesis of 1,1'-Bi-2-naphthol by oxidative coupling of naphthol on mesoporous Fe,Cu/MCM-41 aluminosilicates
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The oxidative coupling of 2-naphtol to 2,2'-dihydroxy-1,1'-binaphthyl (binaphthol) by air or oxygen has been carried out in the presence of Cu2+- and Fe3+-doped MCM-41 aluminosilicate as catalyst. Fe-exchanged MCM-41 was found to be a very efficient catalyst; excellent mass balances (> 95%) with almost total conversion and selectivity to binaphthol were achieved. The same reaction has also been carried out on Cu2+- and Fe3+-Y zeolites. Taking into account the relative dimensions of binaphthol and the catalyst pores, molecular modeling predicts that binaphthol can be accommodated inside the zeolite Y supercages (1.3 nm), but it cannot diffuse outside the zeolite cavities through the smaller pore apertures (0.74 nm). This prediction has been confirmed by dissolving a Y zeolite after the reaction, whereby unextractable binaphthol entrapped within the cavities was recovered. Variable amounts of two secondary by-products have also been detected, and their structure assigned to (2,8');(8,2')-dioxo-1,1'-binaphthyl and bisnaphthofuran based on analytical and spectroscopic data. Their percentage is particularly high when alumina-supported CuSO4 is used as the catalyst.
- Armengol, Elvira,Corma, Avelino,Garcia, Hermenegildo,Primo, Jaime
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p. 1915 - 1920
(2007/10/03)
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