4042-81-3Relevant academic research and scientific papers
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.
Synthesis of benzyl sulfidesviasubstitution reaction at the sulfur of phosphinic acid thioesters
Nishiyama, Yoshitake,Hosoya, Takamitsu,Yoshida, Suguru
, p. 5771 - 5774 (2020/06/03)
An ambident electrophilicity of phosphinic acid thioesters is disclosed. Unexpected carbon-sulfur bond formation took place in the reaction between phosphinic acid thioesters and benzyl Grignard reagents. The developed method for benzyl sulfides has a wide substrate scope and was applicable for the synthesis of a drug analog.
Palladium-catalyzed phosphorylation of benzyl ammonium triflates with P(O)H compounds
Chen, Tieqiao,Huang, Tianzeng,Liu, Long,Wang, Wenqi,Wang, Yuan,Xu, Hanshuang,Xu, Kaiqiang
, (2020/03/03)
A palladium-catalyzed phosphorylation of benzyl ammonium triflates with P(O)H compounds has been developed. Various benzylphosphorus compounds were produced in good to excellent yields with high functional group tolerance. All the three kinds of hydrogen phosphoryl compounds, i.e. H-phosphonates, H-phosphinates and secondary phosphine oxides, were applicable to this reaction. The successful scale-up experiment and one-pot synthetic operation also well demonstrated its practicality.
A Simple Synthesis and Some Synthetic Applications of Substituted Phosphide and Phosphinite Anions
Tsvetkov, E. N.,Bondarenko, N. A.,Malakhova, I. G.,Kabachnik, M. I.
, p. 198 - 208 (2007/10/02)
Based on data for the acidity relationship of phosphines and phosphinous acids and water in dimethyl sulfoxide and water, a simple method is reported for the generation of phosphide and phosphinite anions by the action of concentrated aqueous alkali on primary and secondary phosphines as well as phosphinous acids in dimethyl sulfoxide or other dipolar aprotic solvents.Alkylation of the anion yields secondary and tertiary phosphines, polyphosphines, functionally substituted phosphines as well as similarly substituted phosphine oxides.Phosphinous acids have beenalkylated in various solvents in two-phase systems containing concentrated aqueous alkali and tetrabutylammonium iodide as phase transfer catalyst.
