Silver-Catalyzed Oxyphosphorylation of Unactivated Alkynes

被引:10
作者
Liu, Binbin [1 ]
Song, Qingmin [1 ]
Liu, Zhaohong [1 ]
Wang, Zikun [1 ]
机构
[1] Northeast Normal Univ, Dept Chem, Jilin Prov Key Lab Organ Funct Mol Design & Synth, Changchun 130024, Peoples R China
基金
中国国家自然科学基金;
关键词
Alkynes; Silver-catalyzed; Hydroazidation; beta-Ketophosphine oxides; Pyrroles; H-PHOSPHINE OXIDES; C-H/P-H; VINYL AZIDES; ONE-POT; TERMINAL ALKYNES; METAL-FREE; AEROBIC OXYPHOSPHORYLATION; BETA-KETOPHOSPHONATES; CHEMICAL-SYNTHESIS; FACILE SYNTHESIS;
D O I
10.1002/adsc.202100226
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Here, we describe an application of hydroazidation in the instant activation of alkynes for achieving the oxyphosphorylation of unactivated alkynes with diarylphosphinoyl radicals under mild reaction conditions. This reaction provides a method for accessing beta-ketophosphine oxides and phosphorus-containing pyrroles.
引用
收藏
页码:3214 / 3219
页数:6
相关论文
共 50 条
[31]   Copper-Catalyzed Direct Oxyphosphorylation of Enamides with P(O)-H Compounds and Dioxygen [J].
Liang, Wu ;
Zhang, Zhijie ;
Yi, Dong ;
Fu, Qiang ;
Chen, Suyuan ;
Yang, Lu ;
Du, Fengtian ;
Ji, Jianxin ;
Wei, Wei .
CHINESE JOURNAL OF CHEMISTRY, 2017, 35 (09) :1378-1382
[32]   Silver-catalyzed fluoroalkylation of thiols using fluoroalkanesulfinates [J].
Ma, Jing-jing ;
Liu, Qi-ran ;
Lu, Guo-ping ;
Yi, Wen-bin .
JOURNAL OF FLUORINE CHEMISTRY, 2017, 193 :113-117
[33]   Gold-Catalyzed Intermolecular Hydrophenoxylation of Unactivated Internal Alkynes [J].
Kuram, Malleswara Rao ;
Bhanuchandra, M. ;
Sahoo, Akhila K. .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (07) :2247-2258
[34]   Iron-Catalyzed Oxyphosphorylation of Styrenes to Access β-Ketophosphonates and α, β-Unsaturated Ketones [J].
Zhao, Yukun ;
Xu, Jingwen ;
Chen, Hongbing ;
Xia, Yi ;
Hu, Lin .
ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (19) :3290-3294
[35]   Silver-Catalyzed Oxidative Cyclization of Propargylamide-Substituted Indoles: Synthesis of Phosphorated Indoloazepinones Derivatives [J].
Hua, Hui-Liang ;
Zhang, Bo-Sheng ;
He, Yu-Tao ;
Qiu, Yi-Feng ;
Wu, Xin-Xing ;
Xu, Peng-Fei ;
Liang, Yong-Min .
ORGANIC LETTERS, 2016, 18 (02) :216-219
[36]   Silver-Catalyzed Radical Transformation of Aliphatic Carboxylic Acids to Oxime Ethers [J].
Zhu, Yuchao ;
Wen, Xiaojin ;
Song, Song ;
Jiao, Ning .
ACS CATALYSIS, 2016, 6 (10) :6465-6472
[37]   Silver-Catalyzed Three-Component 1,1-Aminoacylation of Homopropargylamines: α-Additions for Both Terminal Alkynes and Isocyanides [J].
Tong, Shuo ;
Piemontesi, Cyril ;
Wang, Qian ;
Wang, Mei-Xiang ;
Zhu, Jieping .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (27) :7958-7962
[38]   Electrochemical Oxidation-Induced Oxyphosphorylation of Alkenes and Alkynes with Water via Hydrogen Atom Transfer [J].
Yang, Jianjing ;
Sun, Xue ;
Yan, Kelu ;
Sun, Hongzhao ;
Sun, Shuai ;
Jia, Xiaoyu ;
Zhang, Fanjun ;
Wen, Jiangwei .
ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (16) :2735-2740
[39]   Silver-Catalyzed Olefination of Acetals and Ketals with Diazoesters to β-Alkoxyacrylates [J].
Li, Jiawen ;
Qian, Bo ;
Huang, Hanmin .
ORGANIC LETTERS, 2018, 20 (22) :7090-7094
[40]   Silver-Catalyzed Anti-Markovnikov Hydroxyfluorination of Styrenes [J].
Li, Yan ;
Jiang, Xiaohuan ;
Zhao, Chaoyue ;
Fu, Xiaoning ;
Xu, Xiufang ;
Tang, Pingping .
ACS CATALYSIS, 2017, 7 (03) :1606-1609