Phosphorylation of 2-Aryl Quinoxaline Derivatives via C-H/P-H Cross Coupling under Transition-Metal-Free Conditions

被引:1
|
作者
Karimi-Nami, Rahman [1 ]
Adib, Mehdi [2 ]
Heydari, Forouzan [2 ]
Rajai-Daryasarei, Saeideh [2 ]
Karakaya, Idris [3 ]
机构
[1] Univ Maragheh, Fac Sci, Dept Chem, Maragheh, Iran
[2] Univ Tehran, Coll Sci, Sch Chem, Tehran, Iran
[3] Gebze Tech Univ, Coll Basic Sci, Dept Chem, Gebze, Turkey
关键词
Phosphorus-substituted heterocycles; 2-Aryl quinoxalines; dialkyl phosphites; C-H activitaion; RADICAL-ADDITION; BOND FORMATION; FREE ACYLATION; PHOSPHONATION; INHIBITORS; ACCESS; ACID;
D O I
10.1080/10406638.2021.1983619
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In this study, we have developed an efficient protocol for synthesis of phosphorus-substituted heterocycles through reaction between 2-Aryl quinoxalines and dialkyl phosphites under transition-metal-free conditions. Here, K2S2O8 has been used as the sole oxidant for the facile synthesis of phosphorus substituted derivates. A variety of heteroaryl phosphonate derivatives have been synthesized under optimized conditions in good to excellent yields with this facile and environment friendly protocol.
引用
收藏
页码:6411 / 6416
页数:6
相关论文
共 50 条
  • [31] Facile Access to 1H-Indazoles through Iodobenzene-Catalyzed C-H Amination under Mild, Transition-Metal-Free Conditions
    Kashiwa, Mitsuhiro
    Sonoda, Motohiro
    Tanimori, Shinji
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (22) : 4720 - 4723
  • [32] Direct phosphorylation of benzylic C-H bonds under transition metal-free conditions forming sp3C-P bonds
    Li, Qiang
    Zhao, Chang-Qiu
    Chen, Tieqiao
    Han, Li-Biao
    RSC ADVANCES, 2022, 12 (29) : 18441 - 18444
  • [33] Dehydrative allylation of P-H species under metal-free conditions
    Yang, Xiaobo
    Li, Bowen
    Xing, Huicong
    Qiu, Ju
    Loh, Teck-Peng
    Xie, Peizhong
    GREEN CHEMISTRY, 2021, 23 (04) : 1633 - 1637
  • [34] Transition-Metal-Free Lactonization of sp2 C-H Bonds with CO2
    Zhang, Zhen
    Ju, Tao
    Miao, Meng
    Han, Jie-Lian
    Zhang, Yi-Han
    Zhu, Xing-Yong
    Ye, Jian-Heng
    Yu, Da-Gang
    Zhi, Yong-Gang
    ORGANIC LETTERS, 2017, 19 (02) : 396 - 399
  • [35] Synthesis of 2-aryl quinazolinones via iron-catalyzed cross-dehydrogenative coupling (CDC) between N-H and C-H bonds
    Jang, Yoonkyung
    Lee, Seok Beom
    Hong, Junhwa
    Chun, Simin
    Lee, Jeeyeon
    Hong, Suckchang
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (28) : 5435 - 5441
  • [36] Dehydrative Cross-Coupling for C-N Bond Construction under Transition-Metal-Free Conditions
    Xing, Huicong
    Chen, Meijuan
    Zhang, Dong
    Geng, Zhishuai
    Xie, Peizhong
    Loh, Teck-Peng
    ORGANIC LETTERS, 2022, 24 (31) : 5657 - 5662
  • [37] Non-Noble-Metal Mono and Bimetallic Composites for Efficient Electrocatalysis of Phosphine Oxide and Acetylene C-H/P-H Coupling under Mild Conditions
    Tarasov, Maxim V. V.
    Bochkova, Olga D. D.
    Gryaznova, Tatyana V. V.
    Mustafina, Asiya R. R.
    Budnikova, Yulia H. H.
    INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2023, 24 (01)
  • [38] Oxidative cross-coupling of pyridine N-oxides and ethers between C(sp2)-H/C(sp3)-H bonds under transition-metal-free conditions
    Sun, Wei
    Xie, Zuguang
    Liu, Jie
    Wang, Lei
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (15) : 4596 - 4604
  • [39] Direct Synthesis of 2-Aryl-4-quinolones via Transition-Metal-Free Intramolecular Oxidative C(sp3)-H/C(sp3)-H Coupling
    Hu, Wei
    Lin, Jian-Ping
    Song, Li-Rui
    Long, Ya-Qiu
    ORGANIC LETTERS, 2015, 17 (05) : 1268 - 1271
  • [40] Visible-light-initiated regio- and stereoselective C(sp2)-H phosphorylation of enamides under transition-metal-free conditions
    Tao, Ji-Yu
    Zhang, Qing-Hong
    Zhu, Tong-Hao
    Xu, Xin-Wen
    Ni, Kun
    Zhao, Qiao
    Qin, Zheng-Bao
    Zhang, Yu
    Zhao, Lili
    Zhao, Kai
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (23) : 6540 - 6546