- Light-Promoted Nickel Catalysis: Etherification of Aryl Electrophiles with Alcohols Catalyzed by a NiII-Aryl Complex
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A highly effective C?O coupling reaction of (hetero)aryl electrophiles with primary and secondary alcohols is reported. Catalyzed by a NiII-aryl complex under long-wave UV (390–395 nm) irradiation in the presence of a soluble amine base without any additional photosensitizer, the reaction enables the etherification of aryl bromides and aryl chlorides as well as sulfonates with a wide range of primary and secondary aliphatic alcohols, affording synthetically important ethers. Intramolecular C?O coupling is also possible. The reaction appears to proceed via a NiI–NiIII catalytic cycle.
- Cao, Rui,Lai, Chu-Hui,Li, Gang,Liu, Fengyi,Lu, Huan-Huan,Wang, Chao,Xiao, Jianliang,Xue, Dong,Yang, Liu,Zhang, Wei
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supporting information
p. 12714 - 12719
(2020/06/02)
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- Oligo-m-aniline foldamers
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Nitrogen atoms showed intriguing properties such as, they can adopt sp 2 or sp3 electronic configurations and form various degrees of conjugations with the adjacent aromatic rings depending on the electric nature of aromatic rings. T
- Li, Sen,Wang, De-Xian,Wang, Mei-Xiang
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supporting information
p. 6426 - 6429,4
(2012/12/12)
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- Use of diethoxymethane as a solvent for phase transfer-catalyzed O -alkylation of phenols
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The effectiveness of diethoxymethane (DEM) as a solvent for O-alkylation of a variety of phenols under phase transfer conditions has been examined and evaluated. The reaction between 4-methoxy phenol and benzyl chloride was selected to compare reaction rates in various solvents and the efficiency of various PTCs. This reaction was further studied to develop a commercially amenable process complete with recycle streams and efficient product isolation. DEM is a good solvent for these types of phase transfer-catalyzed reactions and can be considered as an alternative solvent for dichloromethane and toluene.
- Coleman, M. Todd,Leblanc, Gabriel
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experimental part
p. 732 - 736
(2011/07/07)
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- Hydrocarbons and chloroaromatics from anilines and n-butyl nitrite
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A single reagent, i.e. n-butyl nitrite, can be used to oxidize an aromatic amine, or the corresponding N-methylene derivative, to a diazo compound followed by its subsequent reduction to hydrocarbon in a single batch.Alternatively, a chloro derivative can be obtained if carbon tetrachloride is used as the solvent.The reactions appear to be general and complete product identification was accomplished.
- Giumanini, Angelo G.,Verardo, Giancarlo,Gorassini, Fausto,Strazzolini, Paolo
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p. 311 - 316
(2007/10/02)
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- T-Butyl-phenoxy-alkylene esters of benzoic and nicotinic acids, compositions containing same and their antihistaminic method of use
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p-Alkyl or cycloalkyl phenoxy alkanols and esters are provided having the structure: STR1 in which: R1 is an alkyl group having from one to six carbon atoms, preferably tertiary, and still more preferably tertiary-butyl; or a bivalent cycloalkylene group condensed with the phenyl group at adjacent ring carbons thereof, such as in indane; R2 is lower alkyl having from one to three carbon atoms or hydrogen; R3 is hydroxyl or an ester group selected from the group consisting of COOR4 and OOCR4 derived from unsubstituted and hydroxy-substituted monocarboxylic acids and COOR5 OOC and OOCR5 COO derived from unsubstituted and hydroxy-substituted dicarboxylic acids, the acids being selected from the group consisting of aliphatic acids, including carbamic acid, having from one to about twelve carbon atoms; cycloaliphatic acids having from three to about twelve carbon atoms; carbocyclic aromatic acids having from six to about twenty carbon atoms; and nitrogen heterocyclic aromatic acids having from five to about twelve carbon atoms, R4 being monovalent aliphatic, cycloaliphatic, aromatic, or nitrogen heterocyclic aromatic, and R5 being divalent aliphatic, cycloaliphatic, aromatic, or nitrogen heterocyclic aromatic, the acids being esterified with aliphatic alcohols having from one to six carbon atoms; and carbonic acid monoalkyl esters, the alkyl having from one to three carbon atoms; and n1, n2 and n3 represent the number of CH2, C(R2)2 and CH2 groups, respectively, and are numbers within the range from 0 to 10; and at least one of n1, n2 and n3 is other than zero. These compounds inhibit abnormal tissue reactivity due to specific allergic hypersensitivity or due to specific irritants by inhibiting the release of chemical mediators that are responsible for the symptoms of allergic diseases, including allergic rhinitis, asthma, hypersensitivity of the skin and of the gastrointestinal canal, and the many symptoms of irritation and inflammation produced by irritants and inflammation-causing substances.
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- Conversion of tertiary amines to formamides in presence of dichlorocarbene and phenoxide ion
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Tertiary amines were found to be a convenient alkyl source for O-alkylation of substituted phenol, in presence of dichlorocarbene in a two-phase system.
- Yonovich, Minda,Sasson, Yoel
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p. 1875 - 1876
(2007/10/02)
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