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Phosphafluorenyl lithiums:direct synthesis from white phosphorus,structure and diversified synthons

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Science China Chemistry 2022年第2期65卷 322-327页

作者： Jingyuan Hu Zhengqi Chai Wei Liu Zhe Huang Junnian Wei Wen-Xiong Zhang Beijing National Laboratory for Molecular Sciences(BNLMS) State Key Laboratory of Rare Earth Materials Chemistry and Applications&Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of EducationCollege of ChemistryPeking UniversityBeijing 100871China

While rich chemistry of phospholyl anions is discovered,phosphafluorenyl anions are only proposed as the critical intermediates for the synthesis of phosphafluorenes.In this article,we reported the direct synthesis of phosphafluorenyl lithiums from white phosphorus(P_(4))through direct P-C bond formation.The reaction between P4 and biphenyl dilithio reagents efficiently afforded phosphafluorenyl lithiums,which were further used to synthesize different kinds of organophosphorus compounds.The aggregation states of phosphafluorenyl lithiums were investigated for the first time.Mechanistic studies by DFT calculations revealed a cooperative nucleophilic attack of two C−Li bonds on P_(4)molecule.

关键词： white phosphorus organophosphorus compounds P–C bond formation P_(4)functionalization phosphafluorenyl lithium

Synthesis of Tetrathiophosphates from white phosphorus

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Chinese Journal of Chemistry 2023年第18期41卷 2311-2316页

作者： Jiali He Shanshan Shi Yumeng Zhang Yang Zhang Pengxiang Xu Guo Tang Yufen Zhao Department of Chemistry College of Chemistry and Chemical Engineeringand the Key Laboratoryfor Chemical Biology of FujianProvinceXiamenUniversityXiamenFujian361005China School of Chemistry and Chemical Engineering Hefei Normal UniversityHefeiAnhui 230601China

Comprehensive Summary,A transition-metal-free one-pot direct synthesis of tetrathiophosphates(R^(1)S)_(2)P(S)SR^(2) from white phosphorus(P_(4)),through intermediate sodium alkyltetrathiophosphates(R^(1)S)_(2)P(S)SNa,is presented.In the presence of NaSH,various disulfides such as diaryl disulfidbges and dialkyl disulfides are easily coupled with P_(4) to give sodium alkyltetrathiophosphates(R^(1)S)_(2)P(S)SNa in almost quantitative yield,which react with alkyl halides in one pot to generate(R^(1)S)_(2)P(S)SR2.Furthermore,S-(2-cyanoethyl)-substituted tetrathiophosphates(R^(1)S)_(2)P(S)SCH_(2)CH_(2)CN are successfully designed as a kind of tetrathiophosphorylation reagent to react with diaryl iodonium salts involving deprotection-dealkylation process.

关键词： white phosphorus Inorganic sulfur Substituted tetrathiophosphate Cross-coupling Nucleophilic substitution Phosphorylation

Uranium(Ⅲ)–phosphorus(Ⅲ) Synergistic Activation of white phosphorus and Arsenic

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CCS Chemistry 2022年第8期4卷 2630-2638页

作者： Wei Fang Iskander Douair Adrian Hauser Kai Li Yue Zhao Peter WRoesky Shuao Wang Laurent Maron Congqing Zhu State Key Laboratory of Coordination Chemistry Jiangsu Key Laboratory of Advanced Organic MaterialsSchool of Chemistry and Chemical EngineeringNanjing UniversityNanjing 210023 LPCNO CNRS&INSAUniversitéPaul SabatierToulouse 31077 Institute of Inorganic Chemistry Karlsruhe Institute of Technology(KIT)Karlsruhe 76131 State Key Laboratory of Radiation Medicine and Protection School for Radiological and Interdisciplinary Sciences(RAD-X)Collaborative Innovation Center of Radiation Medicine of Jiangsu Higher Education InstitutionsSoochow UniversitySuzhou 215123

The study of small-molecule activation by f-block elements still lags far behind that of transition metals.Although a few uranium complexes have been reported to activate dinitrogen,reports on the activation of heavier congeners,such as white phosphorus(P_(4)),by uranium species are extremely rare,and no example of uranium-mediated activation of elemental arsenic has appeared.

关键词： uranium As0 nanoparticle white phosphorus small molecule activation U(Ⅲ)–P(Ⅲ)synergy density functional theory calculations

Direct and chlorine-free synthesis of phosphafluorenes or their oxides from white phosphorus

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Green Synthesis and Catalysis

Green Synthesis and Catalysis 2023年第4期4卷 330-333页

作者： Jingyuan Hu Zhengqi Chai Wei Liu Junnian Wei Ze-Jie Lv Wen-Xiong Zhang Beijing National Laboratory for Molecular Sciences(BNLMS) State Key Laboratory of Rare-earth Materials Chemistry and Applications&Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of EducationCollege of Chemistry and Molecular EngineeringPeking UniversityBeijing 100871China Institute of Inorganic Chemistry University of GöottingenGöottingen 37077Germany

The known methods for the preparation of acylphosphine oxides and polyfluorobenzene-substituted triarylphosphines need to utilize PCl_(3),while the chlorine-free methods are not reported.In this work,we report a chlorine-free method by one-pot three-component reaction of white phosphorus(P_(4)),dilithio reagents,and acyl chlorines or polyfluorobenzenes for the synthesis of biphenyl-based acylphosphine oxides and phosphines.This reaction is green and environmentally friendly compared with the traditional method,because it avoids the use of Cl_(2) and the discharge of a large amount of waste gas and waste acid.These two products have potential applications as photoinitiators in photopolymerization or as organophosphorus ligands in catalytic reactions.

关键词： white phosphorus Dilithio reagents Acylphosphine oxides Triarylphosphines

Direct Functionalization of white phosphorus to Organophosphorus Compounds

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Direct Functionalization of White Phosphorus to Organophosph...

A study on synthesis and oxidation mechanism of mono-alkyl phosphate

中国化学会·第十六届全国有机合成化学学术研讨会

作者：张文雄北京大学

Direct functionalization of white phosphorus(P4) constructing value-added phosphorus-containing compounds is becoming a hot area because it avoids the use of toxic phosphorus halides and phosphine gas. From the view-point of sustainability and green chemistry,the direct and highly efficient construction of P-C bonds from P4 and organic or organometallic substrates is an ideal process.Herein,we report(Scheme 1):i) the reaction of 1,4-dilithio-1,3-butadienes with P4 affording phospholyl lithium quantitatively,3 ii) the [3+1]-fragmentation reaction of rare-earth metallacyclopentadienes with P4 affording rare-earth metal cyclo-P complexes and phospholyl lithium,4 and iii) the reaction of aluminacyclopentadienes with P4 affording selectively cyclotetraphosphanes.

关键词： white phosphorus Organophosphorus compounds Metallacyclopentadiene 1,4-Dilithio-1,3-butadienes

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Journal of Pharmaceutical Analysis 2009年第3期21卷 172-175,188页

作者： Sheng Wang1,Shu-yun Yan2,Qing-guo Ye21. Chinese Research Academy of Environmental Science,Beijing 100012 2.Qingdao University of Science and Technology,Qingdao 266042,China. Chinese Research Academy of Environmental Science Beijing 100012 China Qingdao University of Science and Technology Qingdao 266042 China

Oxidation of white phosphorus by peroxides to produce mono-alkyl phosphate in the alcoholic solution has been studied under non-and catalytic conditions. In this paper,the mechanism of the oxidation process was analyzed. The content of mono-alkyl phosphate in the product is affected by different types of alcoholic solution and peroxide solvent. The result shows the availability of the following order for the activity of the peroxide solvent and alcoholic solutions-tert-butyl hydroperoxide>(di) benzoyl peroxide>hydroperoxide; methanol>n-butyl alcohol>phenol. Under optimized reaction conditions:n(white phosphorus)︰n(tert-butyl hydroperoxide)︰n(methanol)=1︰10︰12,reaction temperature 80 ℃,reaction time 2.5 h,products of 80.0% mono-alkyl phosphonates can be provided when white phosphorus undergoes oxidation by tert-butyl hydroperoxide in the methanol solutions. When Cu(Ⅰ),and Cu(Ⅱ) complexes are used as catalysts,it is possible to significantly enhance the oxidation of white phosphorus with the increase in the reaction rate. The order for activity of catalysts is Cu(acac)2>Cu (CH3COO)2>Cu (C3H7COO)2>CuI>CuCl2. Noticeably,with Cu(acac)2 as catalyst,the selectivity for mono-alkyl phosphonates can reach 95% under adequate reaction conditions.

关键词： white phosphorus pentoxide mono-alkyl phosphate copper