Synthesis of N-methoxy-1 phosphoryloxy imidates through a copper-catalyzed cross-dehydrogenative coupling of N-methoxylamides with phosphites

被引：4

作者：

Deng, Xiangmeng ^{[1
]}

Wang, Ying ^{[1
]}

Liu, Jin-Biao ^{[1
]}

Wan, Changfeng ^{[2
]}

Luo, Nianhua ^{[3
]}

机构：

[1] Jiangxi Univ Sci & Technol, Jiangxi Prov Key Lab Funct Mol Mat Chem, Ganzhou 341000, Peoples R China

[2] Jiangxi Normal Univ, Coll Chem & Chem Engn, Nanchang 330022, Peoples R China

[3] Gannan Med Univ, Sch Pharmaceut Sci, Ganzhou 341000, Peoples R China

来源：

TETRAHEDRON LETTERS | 2022年 / 105卷

基金：

中国国家自然科学基金;

关键词：

Copper catalysis; N-methoxylamide; Phosphite; Cross-dehydrogenative coupling; P-O; H-PHOSPHONATES; GENERAL-METHOD; ALCOHOLS; OXIDES; EFFICIENT; PROTOCOL; AMINES; ESTERS; AMIDES;

D O I：

10.1016/j.tetlet.2022.154049

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Phosphonates are important organic compounds, which are widely used in medicine, materials, agricul-ture and catalysis. In this paper, we report a copper-catalyzed cross-dehydrogenative coupling of N- methoxamides with various phosphites to synthesize a series of N-methoxy-1 phosphoryloxy imidates. O-Functionalization of N-methoxamides has been achieved, and N-functionalization was avoided by employing this methodology. Studies show that the N-methoxy group is essential for the selectivity and activity of the reaction. (c) 2022 Elsevier Ltd. All rights reserved.

引用

页数：5

共 50 条

[41] Computational Studies on the Mechanism of the Copper-Catalyzed sp3-C-H Cross-Dehydrogenative Coupling Reaction
Cheng, Gui-Juan
Song, Li-Juan
Yang, Yun-Fang
Zhang, Xinhao
Wiest, Olaf
Wu, Yun-Dong
CHEMPLUSCHEM, 2013, 78 (09): : 943 - 951
[42] Copper(ii)-catalyzed synthesis of multisubstituted indoles through sequential Chan-Lam and cross-dehydrogenative coupling reactions
Chen, Xin
Bian, Yunyun
Mo, Baichuan
Sun, Peng
Chen, Chunxia
Peng, Jinsong
RSC ADVANCES, 2020, 10 (42) : 24830 - 24839
[43] Copper-Catalyzed Cross-Dehydrogenative C-N Bond Formation of Azines with Azoles: Overcoming the Limitation of Oxidizing N-O Activation Strategy
Sun, Kai
Wang, Xin
Liu, Lulu
Sun, Jingjing
Liu, Xin
Li, Zhenduo
Zhang, Zhiguo
Zhang, Guisheng
ACS CATALYSIS, 2015, 5 (12): : 7194 - 7198
[44] Photocatalytic cross-dehydrogenative coupling reaction toward the synthesis of N,N-disubstituted hydrazides and their bromides
Zheng, Lvyin
Zhuo, Xiaoya
Wang, Yihan
Zou, Xiaoying
Zhong, Yumei
Guo, Wei
ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (11): : 3012 - 3021
[45] Copper-Catalyzed and Air-Mediated Mild Cross-Dehydrogenative Coupling of Aryl Thioureas and Dialkyl H-Phosphonates: The Synthesis of Thiophosphonates
Chang, Cai-Zhu
Liu, Xing
Zhu, Hui
Wu, Li
Dong, Zhi-Bing
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (21): : 13530 - 13535
[46] Iron-catalyzed cross-dehydrogenative C-N coupling of thiohydantoins with various amines
Mudaliar, Sulochana S.
Patel, Anuj P.
Patel, Janki J.
Chikhalia, Kishor H.
TETRAHEDRON LETTERS, 2018, 59 (08) : 734 - 738
[47] Synthesis of N-aryl-D-glucosamines through copper-catalyzed C-N coupling
Tao, Chuanzhou
Liu, Feng
Liu, Weiwei
Zhu, Youmin
Li, Yafeng
Liu, Xiaolang
Zhao, Jing
TETRAHEDRON LETTERS, 2012, 53 (52) : 7093 - 7096
[48] Synthesis of N-Pyridyl Hydroxylamines via Copper-Catalyzed Cross-Coupling
Torruellas, Carilyn
Hsu, Fu-Lian
Walz, Andrew J.
SYNTHESIS-STUTTGART, 2019, 51 (15): : 2891 - 2896
[49] Copper-catalyzed acyloxylation of the C(sp3)-H bond adjacent to an oxygen by a cross-dehydrogenative coupling approach
Raju, Kammari Bal
Kumar, Bejjanki Naveen
Nagaiah, Kommu
RSC ADVANCES, 2014, 4 (92) : 50795 - 50800
[50] Synthesis of Pyrrole-Annulated Heterocycles through Copper-Catalyzed Site-Selective Dehydrogenative Cross-Coupling
Tripathi, Krishna N.
Ray, Devalina
Singh, Ravi P.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (38) : 5809 - 5813

← 1 2 3 4 5 →