61424-52-0Relevant 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.
Palladium-catalyzed C(sp3)–P(III) bond formation reaction with acylphosphines as phosphorus source
Zhang, Mengyue,Ma, Zhichao,Du, Hongguang,Wang, Zhiqian
supporting information, (2020/06/29)
Palladium-catalyzed C(sp3)–P(III) bond formation reaction for alkyl substituted phosphines preparation was developed. In this reaction, various alkyl bromides and limited alkyl chlorides reacted with acylphosphine under relative mild and easily accessible condition, and differential phosphines were afforded in good yields. This reaction made up the application of palladium catalysis in C(sp3)–P(III) bond formation, and indicated a practical application of acylphosphine as a phosphination reagent.
Controllable phosphorylation of thioesters: Selective synthesis of aryl and benzyl phosphoryl compounds
Xu, Kaiqiang,Liu, Long,Li, Zhaohui,Huang, Tianzeng,Xiang, Kang,Chen, Tieqiao
, p. 14653 - 14663 (2020/12/29)
The controllable phosphorylations of thioesters were developed. When the reaction was catalyzed by a palladium catalyst, aryl or alkenyl phosphoryl compounds were generated through decarbonylative coupling, while the benzyl phosphoryl compounds were produced through deoxygenative coupling when the reaction was carried out in the presence of only a base.
Selective C-P(O) Bond Cleavage of Organophosphine Oxides by Sodium
Zhang, Jian-Qiu,Ikawa, Eiichi,Fujino, Hiroyoshi,Naganawa, Yuki,Nakajima, Yumiko,Han, Li-Biao
, p. 14166 - 14173 (2020/11/13)
Sodium exhibits better efficacy and selectivity than Li and K for converting Ph3P(O) to Ph2P(OM). The destiny of PhNa co-generated is disclosed. A series of alkyl halides R4X and aryl halides ArX all react with Ph2P(ONa) to produce the corresponding phosphine oxides in good to excellent yields.
Copper-catalyzed C–P cross-coupling of arylmethyl quaternary ammonium salts via C–N bond cleavage
Li, Nutao,Chen, Feng,Wang, Guanghui,Zeng, Qingle
, p. 99 - 106 (2020/01/06)
Abstract: A ligand-free copper-catalyzed C–P cross-coupling reaction of arylmethyl quaternary ammonium salts and diarylphosphine oxides in air is developed. Arylmethyl quaternary ammonium salts with various functional groups and a variety of dialkyl- and diarylphosphine oxides afford C–P cross-coupling products with good yields. This protocol requires no inert atmosphere, no ligand, and simple operation steps. Graphic abstract: [Figure not available: see fulltext.].
Practical way for the synthesis of phosphine oxides and phosphine sulfides from benzyl alcohol derivatives
Ma, Yutao,Chen, Feng,Bao, Jifeng,Wei, Hao,Shi, Min,Wang, Feijun
supporting information, p. 2465 - 2467 (2016/05/24)
The reaction of benzyl alcohol derivatives with Ph2PI generated in situ from Ph2PCl and NaI provides a facile way to the synthesis of pentavalent phosphine compounds with moderate to excellent yields.
Ph2PI as a reduction/phosphination reagent: Providing easy access to phosphine oxides
Wang, Feijun,Qu, Mingliang,Chen, Feng,Xu, Qin,Shi, Min
, p. 8580 - 8582 (2012/09/22)
The reaction of aldehydes with Ph2PI provides a facile way to the synthesis of pentavalent phosphine compounds with moderate to good yields.
Expedient synthesis of substituted (diphenylphosphinoylmethyl)benzenes
Bew, Sean P.,Brimage, Rebecca A.,Hughes, David L.,Legentil, Laurent,Sharma, Sunil V.,Wilson, Martin A.
, p. 2655 - 2658 (2007/10/03)
An efficient protocol for the synthesis of structurally diverse (diphenylphosphinoylmethyl)benzenes is described. The reaction employs readily available carboxylic acids, chlorodiphenylphosphine, and water as the reagents. A 97% reduction in the reaction
Preparation of aromatic phosphine oxides by reaction of diarylhalophosphine and benzylic halide
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, (2008/06/13)
Phosphine oxides of the formula SPC1 Wherein Ar is a mono- or di-carbocyclic aromatic radical which may be substituted by up to 5 substituents selected from the group consisting of halogen and alkyl of 1 to 3 carbon atoms, Z is halogen or alkyl of 1 to 3 carbon atoms, n is a whole number from 1 to 3, m is a whole number from 0 to 5, and n + m is a whole number from 1 to 6, are prepared by reacting 1. a benzylic halide of the formula SPC2 Wherein X is chlorine, bromine or iodine; and Z, n and m are as specified above, 2. a diarylhalophosphine of the formula wherein Ar is as specified above, and X' is chlorine, bromine or iodine, and 3. an alkali metal hydroxide or an alkaline earth metal hydroxide.
