37086-84-3Relevant articles and documents
Reduction of aryl halides at transition metal cathodes. Conditions for aryl-aryl bond formation: The Ullmann's reaction revisited
Jouikov, Viatcheslav,Simonet, Jacques
, p. 781 - 783 (2010)
The cathodic reduction of some aryl halides ArX (1-naphthyl halides NpI and NpBr, iodo benzene and bromobenzene PhI and PhBr taken as model substrates) was achieved essentially in propylene carbonate (PC) considered for its high dielectric permittivity. Different electrode materials such as copper, silver, palladium, silver palladium alloy and nickel were used. Such conditions permit the activation of the C-X bond by metal (the step featuring similarity with Ullmann's reaction). Electron transfer to organometallic intermediates generated at the metal interface activates the formation of Ar-Ar linkages often in good yields, especially in the case of aryl iodides.
Fast Addition of s-Block Organometallic Reagents to CO2-Derived Cyclic Carbonates at Room Temperature, Under Air, and in 2-Methyltetrahydrofuran
Elorriaga, David,de la Cruz-Martínez, Felipe,Rodríguez-álvarez, María Jesús,Lara-Sánchez, Agustín,Castro-Osma, José Antonio,García-álvarez, Joaquín
, p. 2084 - 2092 (2021/04/02)
Fast addition of highly polar organometallic reagents (RMgX/RLi) to cyclic carbonates (derived from CO2 as a sustainable C1 synthon) has been studied in 2-methyltetrahydrofuran as a green reaction medium or in the absence of external volatile organic solvents, at room temperature, and in the presence of air/moisture. These reaction conditions are generally forbidden with these highly reactive main-group organometallic compounds. The correct stoichiometry and nature of the polar organometallic alkylating or arylating reagent allows straightforward synthesis of: highly substituted tertiary alcohols, β-hydroxy esters, or symmetric ketones, working always under air and at room temperature. Finally, an unprecedented one-pot/two-step hybrid protocol is developed through combination of an Al-catalyzed cycloaddition of CO2 and propylene oxide with the concomitant fast addition of RLi reagents to the in situ and transiently formed cyclic carbonate, thus allowing indirect conversion of CO2 into the desired highly substituted tertiary alcohols without need for isolation or purification of any reaction intermediates.
Benzoxaborole Catalyst for Site-Selective Modification of Polyols
Kusano, Shuhei,Miyamoto, Shoto,Matsuoka, Aki,Yamada, Yuji,Ishikawa, Ryuta,Hayashida, Osamu
supporting information, p. 1598 - 1602 (2020/02/11)
The site-selective modification of polyols bearing several hydroxyl groups without the use of protecting groups remains a significant challenge in synthetic chemistry. To address this problem, novel benzoxaborole derivatives were designed as efficient catalysts for the highly site-selective and protecting-group-free modification of polyols. To identify the effective substituent groups enhancing the catalytic activity and selectivity, a series of benzoxaborole catalysts 1a–k were synthesized. In-depth analysis for the substituent effect revealed that 1i–k, bearing multiple electron-withdrawing fluoro- and trifluoromethyl groups, exhibited the greatest catalytic activity and selectivity. Moreover, 1i-catalyzed benzoylation, tosylation, benzylation, and glycosylation of various cis-1,2-diol derivatives proceeded with good yield and site-selective manner.
