- Visible light induced hydrophosphinylation of unactivated alkenes catalyzed by salicylaldehyde
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An air and water insensitive visible light induced hydrophosphinylation of unactivated alkenes is reported. A small amount of a simple and cheap compound, salicylaldehyde, is used as a photosensitizer. The reaction is carried out in a basic aqueous solution which enables the deprotonated salicylaldehyde to show visible light absorption.
- Cao, Peng,Chen, Tian,Fan, Jiaye,Hu, Ping,Li, Miaomiao,Li, Qianggen,Li, Yang,Wang, Bi-Qin,Wang, Simin,Xiong, Fuying,Yuan, Zeqin
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supporting information
p. 3600 - 3606
(2021/06/06)
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- Photoinduced selective hydrophosphinylation of allylic compounds with diphenylphosphine oxide leading to γ-functionalized P-ligand precursors
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A series of bifunctional phosphine compounds promising as γ-functionalized phosphine ligand precursors are conveniently synthesized by the radical addition of diphenylphosphine oxide (Ph2P(O)H) to allylic compounds under photoirradiation. The p
- Tran, Dat Phuc,Sato, Yuki,Yamamoto, Yuki,Kawaguchi, Shin-ichi,Kodama, Shintaro,Nomoto, Akihiro,Ogawa, Akiya
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p. 3067 - 3078
(2021/04/19)
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- Preparation method of arylalkyl phosphorus oxide compounds
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A preparation method of arylalkyl phosphorus oxide compounds is provided. The invention discloses a preparation method of several arylalkyl phosphorus oxide compounds. The preparation method includes:taking diphenylphosphine oxyhydrogen of 1.3 equivalent, 2.5% by mass nickel catalyst (with or without ligands) or palladium catalyst with ligands and a base of 1.5 equivalent from a glovebox, addingthem sequentially into a Schlenk reaction tube, adding a nitrile compound of 1.0 equivalent, vacuumizing, and backfilling with nitrogen; in the nitrogen atmosphere, adding a solvent, and allowing reaction to occur continuously at 120 DEG C for 16 h; after reaction, cooling to room temperature, and performing column chromatography separation to obtain the target product under high selectivity and high yield. The preparation method herein allows sp3C-CN\P-H cross coupling; reaction conditions are mild; operating is easy; the preparation process is simple; the target product has high conversion rate and high yield; the problems of other synthetic methods are solved that, for instance, two-step reaction system is complex, many organic and inorganic byproducts are produced, environmental pollution is caused easily, and the substrate range is narrow; the preparation method has a good industrial application prospect.
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Paragraph 0086; 0087
(2019/04/09)
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- Catalytic sp3C-CN Bond Cleavage: Ni-Mediated Phosphorylation of Alkylnitriles
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A direct phosphorylation of the sp3C-CN bond catalyzed by a nickel catalyst is disclosed. A wide range of primary nitriles readily coupled with secondary phosphine oxides to produce the corresponding phosphorylated products in high yields. As a key step, this new method was applied to the synthesis of anticancer drug Combretastatin-A4, significantly shortening its synthetic path.
- Zhang, Ji-Shu,Chen, Tieqiao,Zhou, Yongbo,Yin, Shuang-Feng,Han, Li-Biao
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supporting information
p. 6746 - 6749
(2018/10/25)
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- Dearylation of arylphosphine oxides using a sodium hydride-iodide composite
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A new protocol for the dearylation of arylphosphine oxides was developed using sodium hydride (NaH) in the presence of lithium iodide (LiI). The transient sodium phosphinite could be functionalized with a range of electrophiles in a one-pot fashion.
- Tejo, Ciputra,Pang, Jia Hao,Ong, Derek Yiren,Oi, Miku,Uchiyama, Masanobu,Takita, Ryo,Chiba, Shunsuke
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supporting information
p. 1782 - 1785
(2018/02/21)
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- Phosphinoyl Radical Initiated Vicinal Cyanophosphinoylation of Alkenes
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A double-functionalization reaction of alkenes through Mn(OAc)3-mediated phosphinoyl radical addition followed by CuCN-catalyzed cyanation is introduced. This one-pot reaction is performed under mild conditions to afford vicinal cyanophosphinoylation products.
- Zhang, Pei-Zhi,Zhang, Ling,Li, Jian-An,Shoberu, Adedamola,Zou, Jian-Ping,Zhang, Wei
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supporting information
p. 5537 - 5540
(2017/10/25)
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- Catalyst- and solvent-free hydrophosphination and multicomponent hydrothiophosphination of alkenes and alkynes
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The hydrophosphination of carbon-carbon multiple bonds has been generally performed under acid, base or metal catalysis in different solvents. Herein, alkyl and alkenyl tertiary phosphines are obtained by the addition of diphenylphosphine to alkenes and alkynes, respectively, in the absence of a solvent and a catalyst. In the presence of elemental sulfur, the corresponding alkyl and alkenyl tertiary phosphine sulfides are synthesized in a three-component process. These simple methods, which meet most of the principles of Green Chemistry, are highly regioselective towards the anti-Markovnikov products and diastereoselective towards the Z alkenyl phosphines. The mechanistic aspects of the reactions are also tackled and the efficiency of the latter is compared with that of the catalytic methods.
- Moglie, Yanina,González-Soria, María José,Martín-García, Iris,Radivoy, Gabriel,Alonso, Francisco
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supporting information
p. 4896 - 4907
(2016/10/06)
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- Solvent-controlled direct radical oxyphosphorylation of styrenes mediated by Manganese(III)
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Direct radical oxyphosphorylation of styrenes with diarylphosphine oxides and dialkyl phosphites mediated by Mn(OAc)3 is described. The solvent played a key role in this selective difunctionalization reaction.
- Zhang, Guo-Yu,Li, Cheng-Kun,Li, Da-Peng,Zeng, Run-Sheng,Shoberu, Adedamola,Zou, Jian-Ping
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p. 2972 - 2978
(2016/05/19)
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- Direct radical acetoxyphosphorylation of styrenes mediated by manganese(III)
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Direct radical acetoxyphosphorylation of styrenes mediated by Mn(OAc)3 with diphenylphosphine oxide and dialkyl phosphites was described, and a new type of difunctionalization of alkenes was achieved.
- Zhou, Shao-Fang,Li, Da-Peng,Liu, Kui,Zou, Jian-Ping,Asekun, Olayinka Taiwo
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p. 1214 - 1220
(2015/01/30)
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- Copper-catalyzed allylic C-H phosphonation
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An efficient copper-catalyzed allylic C-H phosphonation reaction has been developed under mild reaction conditions. This method exhibits high regioselectivity and stereoselectivity. Various alkenes with useful functional groups are compatible in this tran
- Yang, Bin,Zhang, Hong-Yu,Yang, Shang-Dong
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supporting information
p. 3561 - 3565
(2015/03/30)
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- Copper-catalyzed synthesis of alkylphosphonates from H-phosphonates and N-tosylhydrazones
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A new catalytic system for the alkylation of H-phosphonates and diphenylphosphine oxide with N-tosylhydrazones has been developed. In the presence of copper(I) iodide and base, H-phosphonates react with N-tosylhydrazones to afford the corresponding coupled alkylphosphonates in good to excellent yields without any ligands. Alkylphosphonates can also be prepared in a one-pot process directly from carbonyl compounds without the isolation of tosylhydrazone intermediates.
- Miao, Wenjun,Gao, Yuzhen,Li, Xueqin,Gao, Yuxing,Tang, Guo,Zhao, Yufen
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p. 2659 - 2664
(2013/01/15)
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- 1-DIPHENYLPHOSPHINYL-2,2-DIMETHYLAZIRIDINE - A NEW PRECURSOR OF α,α-DIMETHYLARYLALKYLAMINES
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The new synthesis of α,α-dimethylarylalkylamines from 1-diphenylphosphinyl-2,2-dimethylaziridine is described.
- Buchowiecki, Wieslaw,Grosman-Zjawiona, Zofia,Zjawiony, Jordan
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p. 1245 - 1248
(2007/10/02)
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- Thiol Esters from Sulfoxides via Rearrangement of Sulfoxide Phosphines to Sulfide Phosphine Oxides
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Treatment of α-lithio sulfoxides with (1) ClP-(C6H5)2 and (2) I2 (isolate sulfide phosphine oxide 3) followed by (3) C4H9Li and (4) O2 affords thiol esters.
- Vedejs, E.,Mastalerz, H.,Meier, G. P.,Powell, D. W.
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p. 5253 - 5254
(2007/10/02)
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