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

[1] Transition-Metal-Free Aryl-Aryl Cross-Coupling: C-H Arylation of 2-Naphthols with Diaryliodonium Salts
Ghosh, Manoj K.
Rzymkowski, Jan
Kalek, Marcin
CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (41) : 9619 - 9623
[2] The C-OH/P-H dehydrative cross-coupling for the construction of the P-C bond under metal-free conditions
Xie, Peizhong
Wang, Jinyu
Fan, Jing
Liu, Yanan
Wo, Xiangyang
Loh, Teck-Peng
GREEN CHEMISTRY, 2017, 19 (09) : 2135 - 2139
[3] Metal-Free Synthesis of 2-Aryl Quinazolines via Tandem C-H/N-H Bond Functionalization
Yuan, Feixiang
Xie, Shihua
Zhuo, Liang
Wang, Lei
Zhu, Hongjun
CHEMISTRYSELECT, 2021, 6 (15): : 3707 - 3711
[4] Nickel-Catalyzed Phosphorylation of Phenol Derivatives via C-O/P-H Cross-Coupling
Yang, Jia
Xiao, Jing
Chen, Tieqiao
Han, Li-Biao
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (09) : 3911 - 3916
[5] Transition-metal-free phosphorylation of polyfluoroarenes with P(O)H compounds
Sun, Bingqian
Liang, Yu-Ting
Xiang, Meng-Ting
Ai, Jun-Tao
Wang, Shuai
Zhong, Hong
Yang, Jia
Xiang, Hao-Yue
ORGANIC & BIOMOLECULAR CHEMISTRY, 2025, 23 (10) : 2358 - 2361
[6] Transition-Metal-Free, Formal C-H Germylation of Arenes and Styrenes via Dibenzothiophenium Salts
Selmani, Aymane
Schoenebeck, Franziska
ORGANIC LETTERS, 2021, 23 (12) : 4779 - 4784
[7] 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
[8] 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
[9] Electrochemically dehydrogenative C-H/P-H cross-coupling: effective synthesis of phosphonated quinoxalin-2(1H)-ones and xanthenes
Li, Ke-Jing
Jiang, Yang-Ye
Xu, Kun
Zeng, Cheng-Chu
Sun, Bao-Guo
GREEN CHEMISTRY, 2019, 21 (16) : 4412 - 4421
[10] 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)

← 1 2 3 4 5 →