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

来源：

POLYCYCLIC AROMATIC COMPOUNDS | 2022年 / 42卷 / 09期

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

页码：6411 / 6416

页数：6

共 50 条

[21] Three-component 2-aryl substituted benzothiophene formation under transition-metal free conditions
Jiang, Pengcheng
Che, Xingzong
Liao, Yunfeng
Huang, Huawen
Deng, Guo-Jun
RSC ADVANCES, 2016, 6 (48) : 41751 - 41754
[22] Direct C-H aminocarbonylation of N-heteroarenes with isocyanides under transition metal-free conditions
Zhou, Zhong
Ji, Huihui
Li, Qing
Zhang, Qian
Li, Dong
ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (13) : 2917 - 2922
[23] Copper-Catalyzed Radical/Radical Csp3-H/P-H Cross-Coupling: α-Phosphorylation of Aryl Ketone O-Acetyloximes
Ke, Jie
Tang, Yuliang
Yi, Hong
Li, Yali
Cheng, Yongde
Liu, Chao
Lei, Aiwen
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (22) : 6604 - 6607
[24] Photocatalytic Transition-Metal-Free Direct 3-Acetalation of Quinoxaline-2(1H)-ones
Ma, Chunhua
Meng, Hui
Li, Jing
Yang, Xianguang
Jiang, Yuqin
Yu, Bing
CHINESE JOURNAL OF CHEMISTRY, 2022, 40 (22) : 2655 - 2662
[25] The Stabilized Cation Pool Method: Metal- and Oxidant-Free Benzylic C-H/Aromatic C-H Cross-Coupling
Hayashi, Ryutaro
Shimizu, Akihiro
Yoshida, Jun-ichi
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (27) : 8400 - 8403
[26] Transition-metal-free regioselective C-H halogenation of imidazo[1,2-a] pyridines: sodium chlorite/bromite as the halogen source
Li, Junxuan
Tang, Jiayi
Wu, Yuanheng
He, Qiuxing
Yu, Yue
RSC ADVANCES, 2018, 8 (09): : 5058 - 5062
[27] Nickel-catalysed P-C bond formation via P-H/C-CN cross coupling reactions
Zhang, Ji-Shu
Chen, Tieqiao
Yang, Jia
Han, Li-Biao
CHEMICAL COMMUNICATIONS, 2015, 51 (35) : 7540 - 7542
[28] Silver-Mediated Phosphonylation of C(sp2)-H Bonds with P-H Bonds: Direct C-H Functionalization of Ferrocenyl Anilides and Dialkyl Phosphites under Palladium- and Copper-Free Conditions
Yu, Xiaoli
Ge, Bingyang
Zhang, Yaxuan
Wang, Xiaoli
Wang, Dawei
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 5 (10) : 1253 - 1259
[29] Metal- and Oxidant-Free Alkenyl C-H/Aromatic C-H Cross-Coupling Using Electrochemically Generated Iodosulfonium Ions
Hayashi, Ryutaro
Shimizu, Akihiro
Davies, Jonathan A.
Ishizaki, Yu
Willis, Chris
Yoshida, Jun-ichi
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (39) : 12891 - 12895
[30] Transition-metal-free C-H oxidative activation: persulfate-promoted selective benzylic mono- and difluorination
Ma, Jing-jing
Yi, Wen-bin
Lu, Guo-ping
Cai, Chun
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (10) : 2890 - 2894

← 1 2 3 4 5 →