15367-77-8Relevant academic research and scientific papers
Direct C4-H phosphonation of 8-hydroxyquinoline derivatives employing photoredox catalysis and silver catalysis
Su, Xiaoxue,Yang, Fan,Wu, Yusheng,Wu, Yangjie
, p. 2753 - 2756 (2018)
A simple and efficient protocol for the C4-H phosphonation of 8-hydroxyquinoline derivatives was developed under a photoredox/silver(i) cocatalysis system, providing a new approach to phosphonated 8-hydroxyquinoline derivatives. Note that the reaction did not occur at the C5 site, but regioselectively at an unusual C4 site. Moreover, the reaction proceeded smoothly under mild reaction conditions (a catalytic amount of silver salt and room temperature) with good functional group compatibility.
Silver-mediated radical phosphorylation/cyclization of: N -allylbenzamides to access phosphoryl-substituted dihydroisoquinolones
Liu, Xiao-Ceng,Sun, Kai,Lv, Qi-Yan,Chen, Xiao-Lan,Sun, Yuan-Qiang,Peng, Yu-Yu,Qu, Ling-Bo,Yu, Bing
, p. 12221 - 12224 (2019)
A silver-mediated phosphorylation/cyclization of N-allylbenzamides with phosphine oxides for the synthesis of phosphoryl-substituted dihydroisoquinolones was developed. This protocol features broad substrate scope, experimental simplicity, high efficiency
Visible-Light-Promoted Transition-Metal-Free Approach toward Phosphoryl-Substituted Dihydroisoquinolones via Cascade Phosphorylation/Cyclization of N-Allylbenzamides
Liu, Xiao-Ceng,Sun, Kai,Chen, Xiao-Lan,Wang, Wen-Fei,Liu, Yan,Li, Qian-Li,Peng, Yu-Yu,Qu, Ling-Bo,Yu, Bing
, p. 3712 - 3717 (2019)
A transition-metal-free visible-light-promoted radical phosphorylation/cyclization of N-allylbenzamides with phosphine oxides for the synthesis of phosphoryl-substituted dihydroisoquinolones was developed under room temperature. This protocol features mil
Copper-Catalyzed Vicinal Cyano-, Thiocyano-, and Chlorophosphorylation of Alkynes: A Phosphinoyl Radical-Initiated Approach for Difunctionalized Alkenes
Li, Cheng-Kun,Li, Jian-An,Shoberu, Adedamola,Tao, Ze-Kun,Zhang, Wei,Zou, Jian-Ping
supporting information, p. 4342 - 4347 (2021/06/28)
A copper-catalyzed difunctional cyano-, thiocyano-, and chlorophosphorylation reaction of alkynes with P(O)-H compounds and coupling partners (TBACN, TMSNCS, TMSCl) is described. The reaction introduces versatile groups (-P(O)R2 and -CN, -SCN, or -Cl) to form tri- and tetrasubstituted alkenyl phosphine oxides/phosphonates regio- and stereoselectively.
Visible light induced radical cascade cyclization of: Ortho -cyanoarylacrylamides with phosphine oxides for the preparation of phosphorylated quinoline-2,4(1 H,3 H)-dione
Han, Qing-Qing,Song, Jing-Cheng,Sun, Yuan-Yuan,Wang, Zu-Li,Yang, Shao-Hui,Yue, Shan,Zhang, En-Xuan
, p. 16438 - 16441 (2021/10/01)
Visible light induced cascade cyclization of ortho-cyanoarylacrylamides with phosphine oxides for the preparation of phosphorylated quinoline-2,4(1H,3H)-dione. Products with moderate to good yields were efficiently isolated. A radical mechanism was propos
Manganese(iii)-promoted tandem phosphinoylation/cyclization of 2-arylindoles/2-arylbenzimidazoles with disubstituted phosphine oxides
Jiang, Shuai-Shuai,Li, Jin-Heng,Luo, Shu-Zheng,Song, Ren-Jie,Wu, Yan-Chen,Xiao, Yu-Ting
, p. 4843 - 4847 (2020/07/13)
A simple and practical method for the synthesis of phosphoryl-substituted indolo[2,1-a]isoquinolin-6(5H)-ones and benzimidazo[2,1-a]isoquinolin-6(5H)-ones through manganese(iii)-promoted tandem phosphinoylation/cyclization of 2-arylindoles or 2-arylbenzimidazoles with disubstituted phosphine oxides was developed. In this transformation, new C-P bond and C-C bond were constructed simultaneously under silver-free conditions, exhibiting a broad substrate scope. It was noted that not only diarylphosphine oxides but also dialkyl and arylalkyl-phosphine oxides were compatible with the conditions. This journal is
Proton-Coupled Electron Transfer Enables Tandem Radical Relay for Asymmetric Copper-Catalyzed Phosphinoylcyanation of Styrenes
Zhang, Guoyu,Fu, Liang,Chen, Pinhong,Zou, Jianping,Liu, Guosheng
supporting information, p. 5015 - 5020 (2019/09/03)
A tandem radical relay strategy was realized for the first Cu(I)-catalyzed enantioselective phosphinocyanation of styrenes. In this reaction, tBuOOSiMe3 generated in situ from tBuOOH serves as a radical initiator to trigger t-butoxy radical production upon oxidization of L?Cu(I) species via proton-coupled-electron transfer (PCET) pathway, which leads to sequential phosphinoyl radical and benzyl radical formations. The resultant β-cyanodiarylphosphine oxides could be easily converted to a series of chiral ?-amino phosphine ligands.
Silver-Catalyzed Radical Arylphosphorylation of Unactivated Alkenes: Synthesis of 3-Phosphonoalkyl Indolines
Liang, Deqiang,Ge, Dandan,Lv, Yanping,Huang, Wenzhong,Wang, Baoling,Li, Weili
, p. 4681 - 4691 (2018/04/26)
A silver-catalyzed phosphorylation/cyclization cascade of N-allyl anilines was developed, allowing direct access to 3-phosphonoalkyl indolines, which were previously obtainable only via tedious procedures under harsh/toxic conditions. The unactivated double bond serves as the radical acceptor, whereas H-phosphonates or -phosphine oxides act as the radical precursor. This protocol features simple operation, broad substrate scope, and great exo selectivity, and a gram-scale synthesis could be readily carried out.
Regioselective Direct C3-Phosphorylation of N-Sulfonylindoles under Mild Oxidative Conditions
Su, Feng,Lin, Weidong,Zhu, Pengfei,He, Dezhi,Lin, Jianbin,Zhang, Hui-Jun,Wen, Ting-Bin
supporting information, p. 947 - 951 (2017/03/27)
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.).
Addition of phthalimide and acetone to phosphorylated methylene quinones
Gazizov,Tarakanova,Ismagilov,Shamsutdinova,Karimova,Burangulova
, p. 326 - 330 (2016/04/20)
New method for synthesis of phosphorylated methylene quinones via bromination of the sterically hindered phenol [prepared via benzylation of secondary chlorophosphines with 4-(methoxymethyl)-2,6-di-tert-butylphenol] with N-bromosuccinimide followed by dehydrobromination with trimethyl orthoformate has been developed. Tertiary phosphine oxides containing the fragment of sterically hindered phenol and amine or acetonyl group have been synthesized for the first time in the reaction of phosphorylated methylene quinones with N- and C-nucleophiles.
