19962-26-6Relevant academic research and scientific papers
An alternative route for boron phenoxide preparation from arylboronic acid and its application for C[sbnd]O bond formation
Joo, Seong-Ryu,Kim, Seung-Hoi,Lim, In-Kyun
, (2020/08/06)
An efficient synthetic route to benzyl phenyl ether preparation has been successfully developed via a one-pot synthetic protocol utilizing a combination of arylboronic acids, hydrogen peroxide (H2O2), and benzyl halides. The whole procedure consists of two consecutive reactions, formation of boron phenoxide from arylboronic acids and its nucleophilic attack. A simple operation under mild conditions such as room-temperature ionic liquid (choline hydroxide), aerobic environment, and absence of metal- and base-catalysts has been employed. Expansion to utilize benzyl surrogates was also successfully accomplished.
Base-Mediated O-Arylation of Alcohols and Phenols by Triarylsulfonium Triflates
Ming, Xiao-Xia,Tian, Ze-Yu,Zhang, Cheng-Pan
supporting information, p. 3370 - 3379 (2019/11/03)
A mild and efficient protocol for O-arylation of alcohols and phenols (ROH) by triarylsulfonium triflates was developed under transition-metal-free conditions. Various alcohols, including primary, secondary and tertiary, and phenols bearing either electron-donating or electron-withdrawing groups on the aryl rings were smoothly converted to form the corresponding aromatic ethers in moderate to excellent yields. The reactions were conducted at 50 or 80 °C for 24 h in the presence of a certain base and showed good functional group tolerance. The base-mediated arylation with asymmetric triarylsulfonium salts could selectively transfer the aryl groups of sulfoniums to ROH, depending on their inherent electronic nature. The mechanistic studies revealed that the reaction might proceed through the nucleophilic attack of the in situ formed alkoxy or phenoxy anions at the aromatic carbon atoms of the C?S bonds of triarylsulfonium cations to furnish the target products.
Metal-Free C-O Bond Functionalization: Catalytic Intramolecular and Intermolecular Benzylation of Arenes
Bering, Luis,Jeyakumar, Kirujan,Antonchick, Andrey P.
supporting information, p. 3911 - 3914 (2018/07/22)
A catalytic, metal-free intramolecular rearrangement of benzyl phenyl ethers using nitrosonium salt as a catalyst is described. The optimized reaction conditions enabled a catalytic and metal-free Friedel-Crafts alkylation reaction with benzylic alcohols, producing water as the stoichiometric byproduct. A comprehensive scope (>50 examples) for both approaches and application in drug synthesis were demonstrated. Mechanistic studies suggest a Lewis acid-based mechanism for the metal-free Friedel-Crafts reaction.
From insertion to multicomponent coupling: Temperature dependent reactions of arynes with aliphatic alcohols
Thangaraj, Manikandan,Bhojgude, Sachin Suresh,Mane, Manoj V.,Biju, Akkattu T.
supporting information, p. 1665 - 1668 (2016/01/30)
The temperature dependent selectivity switch in the reaction of arynes with aliphatic alcohols in THF has been reported. At -20°C, arynes smoothly insert into the O-H bond of alcohols to form alkyl aryl ethers. Interestingly, at 60°C, a highly selective multicomponent coupling occurs with the solvent THF acting as the nucleophilic trigger affording (4-(alkoxy)butoxy)arenes.
Formation of arf from lpdar(f): catalytic conversion of aryl triflates to aryl fluorides
Watson, Donald A.,Su, Mingjuan,Teverovskiy, Georgiy,Zhang, Yong,Garcia-Fortanet, Jorge,Kinzel, Tom,Buchwaldf, Stephen L.
scheme or table, p. 1661 - 1664 (2010/06/16)
Despite increasing pharmaceutical importance, fluorinated aromatic organic molecules remain difficult to synthesize. Present methods require either harsh reaction conditions or highly specialized reagents, making the preparation of complex fluoroarenes ch
Substituent Dependence of the ?-Acceptor Induced Bond Cleavage Reactions of Benzyl Phenyl Ethers
Penn, John H.,Lin, Zhe
, p. 1554 - 1559 (2007/10/02)
The relative C-O bond cleavage reaction rates (krel) of eight substituted benzyl phenyl ethers (BPE's) have been measured.These C-O bond cleavage reactions were thermally initiated by 2,3-dichloro-5,6-dicyanoquinone (DDQ).The equilibrium constants (K) for charge-transfer complex formation of these BPE's with the electron acceptors DDQ and TCNE in the solvent methylene chloride have also been determined at room temperature.The best correlation of log krel for DDQ reactions has been observed in these reactions.From this data, hydride transfer to DDQ is the rate-determining step of the reaction.
