- Synthetic method of diphenyl thiophosphate compound
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The invention discloses a synthesis method of a diphenyl thiophosphate compound. The preparation method comprises the following steps: by taking thiophenol as a reaction substrate and trichloroisocyanuric acid (TCCA) as an accelerant, reacting the reaction substrate and the accelerant in an organic solvent under the conditions of normal temperature and normal pressure for 10 minutes, then adding alkoxy diphenyl phosphine, continuously reacting for 10 minutes, and after the reaction is finished, carrying out separation treatment to obtain the diphenyl thiophosphate compound. According to the synthesis method disclosed by the invention, the reaction is carried out at normal temperature and normal pressure without special requirements; the reaction time is short; and high product yield is achieved.
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Paragraph 0033-0034
(2020/05/01)
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- An Alternative Metal-Free Aerobic Oxidative Cross-Dehydrogenative Coupling of Sulfonyl Hydrazides with Secondary Phosphine Oxides
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An alternative metal-free, efficient and practical approach for the preparation of phosphinothioates is established via the aerobic oxidative cross-dehydrogenative coupling (CDC) of sulfonyl hydrazides with secondary phosphine oxides catalyzed by tetrabutylammonium iodide (TBAI) in the presence of atmospheric oxygen. The strategy provides an array of diverse phosphinothioates in good to excellent yields. Furthermore, two representative bioactive molecules are synthesized on up to gram scale by utilizing this method.
- Cheng, Feixiang,Liu, Jianjun,Liu, Teng,Yu, Rong,Zhang, Yanqiong
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p. 253 - 262
(2019/12/28)
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- Preparation method of phosphorothioate compound
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The invention discloses a preparation method of a phosphorothioate compound. The preparation method comprises the following steps: under the action of oxygen in air and at the temperature of 60-80 DEGC, taking a copper salt as a catalyst, reacting a thios
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Paragraph 0021-0029
(2019/12/25)
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- Green synthetic method of thiohypophosphate
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The invention relates to a green synthetic method of thiohypophosphate as shown in the formula I as show in the specification, wherein R is phenyl, not more than three methyl or three methoxyl or three halogen substituted phenyl, straight-chain or branch-chain alkyl with no more than six carbon atoms, straight-chain or branch-chain alkenyl with no more then six carbon atoms, straight-chain or branch-chain alkynyl with no more than six carbon atoms and a 3 to 8-member aliphatic ring group; R is phenyl, not more than three methyl or three methoxyl or three halogen substituted phenyl, pyridyl, benzyl, naphthyl and a 3 to 8-member aliphatic ring group; according to the synthetic method, thiohypophosphate is a product directly obtained by enabling N-R thiophthalimide to react with di-R based phosphine oxide with water as a solvent.
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Paragraph 0010-0013
(2019/10/29)
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- Highly atom-economical, catalyst-free, and solvent-free phosphorylation of chalcogenides
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Silica gel promoted, catalyst-free and solvent-free S-P, Se-P and Te-P bond formations are described. A variety of disulfides coupled with diarylphosphine oxides provide the corresponding phosphinothioates in excellent yields. For the first time, diselenides and ditellurides reacted with dialkyl phosphites under catalyst-free conditions to provide the corresponding phosphoroselenoates and phosphorotelluroates, respectively, in good to excellent yields.
- Choudhary, Rakhee,Singh, Pratibha,Bai, Rekha,Sharma, Mahesh C.,Badsara, Satpal Singh
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p. 9757 - 9765
(2019/12/02)
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- Base-controlled Fe(Pc)-catalyzed aerobic oxidation of thiols for the synthesis of S-S and S-P(O) bonds
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Fe(Pc)-Catalyzed aerobic oxidation of thiols for the synthesis of disulfides has been developed under mild reaction conditions. In addition, an aerobic oxidative cross-dehydrogenative coupling (CDC) reaction of thiols with P(O)-H compounds (H-phosphonates and H-phosphine oxide) for the formation of S-P(O) bonds has been demonstrated under the Fe(Pc) catalysis system with a base additive. Control experiments revealed that the use of a base (DIPA) in this system controls the synthetic pathways in which thiophosphates are formed.
- Huang, Hai,Ash, Jeffrey,Kang, Jun Yong
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p. 4236 - 4242
(2018/06/21)
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- Magnetically recyclable Cu-BTC@Fe3O4 composite-catalyzed C(aryl)-S-P bond formation using aniline, P(O)H compounds and sulfur powder
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A Cu-BTC@Fe3O4 composite was prepared and exhibited good catalytic activity toward the synthesis of S-aryl phosphorothioates. The three-component reaction involved the coupling of in situ generated aryl diazonium salts from aniline, R2P(O)H, and sulfur powder, allowing the facile and direct formation of C(aryl)-S-P bonds. A broad scope of substrates survived the reaction conditions to afford the corresponding products in good to excellent yields. Moreover, this heterogeneous catalyst could be magnetically recovered and reused without significant loss of its activity after six cycles.
- Wang, Liang,Yang, Sen,Chen, Le,Yuan, Sheng,Chen, Qun,He, Ming-Yang,Zhang, Zhi-Hui
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p. 2356 - 2361
(2017/07/22)
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- Photoinduced Coupling Reaction of Diphenyl(2,4,6-trimethylbenzoyl)phosphine Oxide with Interelement Compounds: Application to the Synthesis of Thio- or Selenophosphinates
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Diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide (TMDPO) is a radical initiator widely used in the field of macromolecular chemistry, but not often applied in synthetic organic chemistry. We have focused on the use of TMDPO as a phosphorus source in reactions with different E - E compounds, where E - E represents a heteroatom-heteroatom bond, under photoirradiation. Interestingly, the cross-coupling reaction between TMDPO and disulfides or diselenides successfully affords thio- or selenophosphinates and thio- or selenoesters, respectively. The synthesis of series of thio- and selenophosphinates by this photoinduced cross-coupling reaction is demonstrated.
- Sato, Yuki,Kawaguchi, Shin-Ichi,Nomoto, Akihiro,Ogawa, Akiya
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p. 3558 - 3567
(2017/08/16)
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- Metal- and oxidant-free S-P(O) bond construction: Via direct coupling of P(O)H with sulfinic acids
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We have developed a simple and convenient method for S-P(O) bond formation between R2P(O)H and sulfinic acids under metal-, oxidant-, and halogen-free conditions. The current method is compatible with a broad range of substituents on various substrates including halogens and heterocyclic moieties. The synthetic potential of this method was further highlighted by the expeditious synthesis of optically active P-chiral phosphorothioates via stereospecific coupling.
- Moon, Youngtaek,Moon, Yonghoon,Choi, Hangyeol,Hong, Sungwoo
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p. 1005 - 1013
(2017/08/14)
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- Regioselective Direct C3-Phosphorylation of N-Sulfonylindoles under Mild Oxidative Conditions
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The reactions of N-sulfonylindoles with H-phosphine oxides under oxidative conditions give a wide range of C-3 phosphorylated free (NH)-indoles. Several mild oxidants, such as AgNO3, di-tert-butyl peroxide (DTBP), and K2S2O8, can be used to promote this transformation. (Figure presented.).
- Su, Feng,Lin, Weidong,Zhu, Pengfei,He, Dezhi,Lin, Jianbin,Zhang, Hui-Jun,Wen, Ting-Bin
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p. 947 - 951
(2017/03/27)
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- Metal- and base-free reductive coupling reaction of P(O)-H with aryl/alkyl sulfonyl chlorides: a novel protocol for the construction of P-S-C bonds
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Novel and efficient synthesis of S-aryl/alkyl phosphinothioates from P(O)-H and aryl/alkyl sulfonyl chlorides under metal- and base-free conditions is described. This reaction provides an alternative strategy for the construction of P-S-C bonds in moderate to excellent yields. Moreover, this method can be readily applied to gram-scale preparation.
- Wang, Dungai,Zhao, Jinlong,Xu, Weigang,Shao, Changwei,Shi, Zheng,Li, Liang,Zhang, Xinghua
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supporting information
p. 545 - 549
(2017/01/25)
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- Synthesis of P(O)-S organophosphorus compounds by dehydrogenative coupling reaction of P(O)H compounds with aryl thiols in the presence of base and air
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The synthesis method of P(O)-S organophosphorus compounds by dehydrogenative coupling reaction of P(O)H compounds and aryl thiols was developed. The reaction was carried in the presence of a base and air, and exhibited good characters such as metal-free,
- He, Wei,Hou, Xiao,Li, Xinjin,Song, Liang,Yu, Qing,Wang, Zhongwei
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p. 3133 - 3138
(2017/05/08)
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- Dimethyl sulfoxide as a mild oxidant in S-P(O) bond construction: Simple and metal-free approaches to phosphinothioates
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In the presence of dimethyl sulfoxide (DMSO) as a mild oxidant and reaction medium, a simple and efficient protocol has been developed for the preparation of phosphinothioates via oxidative dehydrogenative phosphorylation of thiols with P(O)H compounds. Additionally, a DMSO-mediated oxidative phosphorylation of disulfides is also demonstrated. Notably, these transformations occur efficiently without the help of any transition metal or additive. These reactions are easy to conduct and can be scaled-up, and various phosphinothioates are readily obtained in moderate to excellent yields with excellent chemoselectivity and good functional-group tolerance.
- Sun, Jian-Guo,Weng, Wei-Zhi,Li, Ping,Zhang, Bo
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supporting information
p. 1128 - 1133
(2017/08/18)
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- Direct synthesis of thiophosphates by reaction of diphenylphosphine oxide with sulfonyl chlorides
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A new method for the synthesis of thiophosphates by reductive coupling reaction of diphenylphosphine oxide and sulfonyl chlorides has been developed. The reaction is metal-free and needs no additives, affording various aryl and alkyl substituted thiophosphates in good to excellent yields under mild conditions.
- He, Wei,Wang, Zhiming,Li, Xinjin,Yu, Qing,Wang, Zhongwei
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p. 7594 - 7598
(2016/11/11)
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- Synthesis of S-Aryl Phosphorothioates by Copper-Catalyzed Phosphorothiolation of Diaryliodonium and Arenediazonium Salts
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Green methods for the synthesis of S-aryl phosphorothioates have been developed based on copper-catalyzed multicomponent reactions involving diaryliodonium/arenediazonium salts, elemental sulfur, and R2P(O)H compounds. Most target products are obtained with these two methods in good to high yields at room temperature. These transformations allow the direct formation P-S and C-S bonds in one reaction.
- Zhang, Liangliang,Zhang, Pengbo,Li, Xueqin,Xu, Jian,Tang, Guo,Zhao, Yufen
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p. 5588 - 5594
(2016/07/13)
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- Metal-Free Visible-Light-Mediated Oxidative Cross-Coupling of Thiols with P(O)H Compounds Using Air as the Oxidant
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Visible light along with 5 mol % of rose bengal catalyzes the direct S-P(O) coupling between thiols and P(O)H compounds in the presence of air as the green oxidant. The protocol is operationally simple and amenable to gram-scale synthesis. A variety of S-
- Sun, Jian-Guo,Yang, Hua,Li, Ping,Zhang, Bo
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supporting information
p. 5114 - 5117
(2016/10/14)
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- TBPB-promoted metal-free synthesis of thiophosphinate/phosphonothioate by direct P-S bond coupling
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An efficient method for the direct coupling of thiol/thiophenol with H-phosphine oxides or H-phosphinate esters is reported. Without using any metallic catalyst, the direct sulfur-phosphorus bond coupling reaction was promoted using tert-butyl peroxybenzo
- Wang, Jichao,Huang, Xin,Ni, Zhangqin,Wang, Sichang,Wu, Jun,Pan, Yuanjiang
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p. 314 - 319
(2018/04/16)
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- Copper-promoted oxidative-fluorination of arylphosphine under mild conditions
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An efficient method for the synthesis of phosphoric fluoride via oxidative coupling between hydrophosphine oxide and NaF is reported. DDQ serves as the oxidizing reagent as well as the hydrogen acceptor. The process involves a Cu(ii) catalysis and exhibits great functional group tolerance under mild reaction conditions. the Partner Organisations 2014.
- Liu, Na,Mao, Liu-Liang,Yang, Bin,Yang, Shang-Dong
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supporting information
p. 10879 - 10882
(2014/10/15)
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- Rhodium-catalyzed thiophosphinylation and phosphinylation reactions of disulfides and diselenides
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Alkyl and aryl dithiophosphinates were synthesized by the reaction of disulfides with biphosphine disulfides in the presence of RhH(PPh 3)4 and 1,2-diphenylphosphinoethane (dppe). The catalyst also promoted synthesis of thiophosphinates and selenothiophosphinates from disulfides and diselenides.
- Arisawa, Mieko,Ono, Tetsuya,Yamaguchi, Masahiko
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p. 5669 - 5671
(2007/10/03)
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- Oxidative hydrolysis of phosphorus(V) esters of thiols by peroxymonosulfate ion. Reactions of peroxymonosulfate ion with phosphorus(V) esters of thiols
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Peroxymonosulfate ion, HSO5-, as Oxone, readily converts phosphorus(V) esters of thiols into the phosphorus(V) and sulfonic acids. The esters were Ph2PO·SC6H4R(p) with R=MeO (1a), Me (1b), H (1c), Cl (1d) and NO2 (1e), (EtO)2PO·SPh (2), Ph2OI·SEt (3) and PhPO(OEt)SEt (4). Reactions are first order in each reactant and second-order rate constants, k2, for 1a-e fit the Hammett equation with ρ=-0.46. The rate constants increase markedly with increasing water content of H2O-MeCN, the activation enthalpies are low and the entropies are negative. Despite the low value of -ρ, these esters are much less reactive than thiol ethers, but the rate constants of reactions of these compounds and acyl thiols qualitatively follow the ionization potentials of the ethers and the esters.
- Blasko, Andrei,Bunton, Clifford A.,Kumar, Anurag
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p. 427 - 434
(2007/10/03)
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- THE REACTIONS OF α-ALKOXYALLYLPHOSPHINE OXIDE YLIDES WITH SILICON, SULPHUR AND PHOSPHORUS ELECTROPHILES
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Anions (2), derived from α-methoxyallylphosphine oxides (1), react with silicon, sulphur and phosphorus electrophiles in a highly regioselective fashion to give the products of γ-attack.
- Devchand, Dipak K.,Murray, Alistair W.,Smeaton, Elizabeth
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p. 4635 - 4638
(2007/10/02)
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