613-62-7Relevant articles and documents
Selective O -alkylation of 2-naphthol using phosphonium-based ionic liquid as the phase transfer catalyst
Yadav, Ganapati D.,Tekale, Smruti P.
, p. 722 - 727 (2010)
The selective preparation of O-alkylated aromatic products from substituted phenol and naphthols is challenging. The O-alkylation of 2-naphthol with benzyl chloride has been studied in this work using phosphonium-based ionic liquids as catalysts such as trihexyl(tetradecyl)phosphonium chloride (THTDPC), trihexyl(tetradecyl)phosphonium bromide (THTDPB), trihexyl(tetradecyl) phosphonium decanoate (THTDPD), and trihexyl(tetradecyl)phosphonium hexafluorophosphate (THTDPH). This is a liquid-liquid phase-transfer-catalysed reaction with reuse of catalyst. The effects of various parameters such as agitation speed, various phosphonium-based ionic liquids, phase volume ratio, catalyst concentration, NaOH concentration, mole ratio of starting materials, and temperature were studied systematically to understand the conversion patterns and the selectivity of the desired product. A mechanism of the reaction and a kinetic model are proposed.
Transition-Metal-Free and Base-Promoted Carbon-Heteroatom Bond Formation via C-N Cleavage of Benzyl Ammonium Salts
Liu, Long,Tang, Yuanyuan,Wang, Kunyu,Huang, Tianzeng,Chen, Tieqiao
, p. 4159 - 4170 (2021/03/09)
A facile and general method for constructing carbon-heteroatom (C-P, C-O, C-S, and C-N) bonds via C-N cleavage of benzyl ammonium salts under transition-metal-free conditions was reported. The combination of t-BuOK and 18-crown-6 enabled a wide range of substituted benzyl ammonium salts to couple readily with different kinds of heteroatom nucleophiles, i.e. hydrogen phosphoryl compounds, alcohols, thiols, and amines. Good functional group tolerance was demonstrated. The scale-up reaction and one-pot synthesis were also successfully performed.
Enantioselective Ni-Catalyzed Electrochemical Synthesis of Biaryl Atropisomers
Chen, Song,Chen, Yue-Gang,Gao, Pei-Sen,Liu, Dong,Ma, Hong-Xing,Mei, Tian-Sheng,Qiu, Hui,Shuai, Bin,Wang, Yun-Zhao
, p. 9872 - 9878 (2020/06/27)
A scalable enantioselective nickel-catalyzed electrochemical reductive homocoupling of aryl bromides has been developed, affording enantioenriched axially chiral biaryls in good yield under mild conditions using electricity as a reductant in an undivided cell. Common metal reductants such as Mn or Zn powder resulted in significantly lower yields in the absence of electric current under otherwise identical conditions, underscoring the enhanced reactivity provided by the combination of transition metal catalysis and electrochemistry.