Copper-catalyzed remote C(sp3)-H heteroarylation of N-fluorocarboxamides with azoles

被引：0

作者：

Gao, Shuo ^{[1
]}

Liu, Zilin ^{[1
]}

Li, Siyu ^{[1
]}

Sun, Yingpei ^{[2
]}

Zhao, Mengmeng ^{[1
]}

Guo, Weibo ^{[1
]}

Zhang, Zhen-Hua ^{[1
]}

机构：

[1] Linyi Univ, Sch Chem & Chem Engn, Linyi 276000, Peoples R China

[2] Shandong Luoxin Pharmaceut Grp Stock Co Ltd, Pharmaceut Res Inst, Linyi, Peoples R China

来源：

TETRAHEDRON | 2025年 / 172卷

基金：

中国国家自然科学基金;

关键词：

DIRECT ARYLATION; BONDS; 1,3,4-OXADIAZOLES; FLUORINATION; ALKYLATION;

D O I：

10.1016/j.tet.2025.134451

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general protocol for intermolecular distal C(sp3)-H heteroarylation of N-fluorocarboxamides with azoles under copper catalysis has been accomplished. Notably, both benzylic C(sp3)-H bonds and aliphatic C(sp3)-H bonds in carboxamides could conduct reactions smoothly and exhibited remarkable regioselectivity. This crossdehydrogenative coupling reaction involved a sequential course of amidyl radical generation, 1,5-hydrogen atom transfer (HAT), and heteroarylation steps. This approach was capable of accomplishing the heteroarylation reaction of the distal carbon-hydrogen bonds of amides by simultaneously activating C(sp2)-H and C(sp3)- H, avoiding the utilization of pre-functionalized heteroarenes.

引用

页数：9

共 50 条

[21] Copper-Catalyzed Sequential C(sp2)/C(sp3)-H Amination of 2-Vinylanilines with N-Fluorobenzenesulfonimide [J].

Cao, Wen-Bin ;

Xu, Xiao-Ping ;

Ji, Shun-Jun .

ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (08) :1771-1776

[22] Benzylic C(sp3)-H Functionalization via Copper-Catalyzed [3+3] Radical Cycloaddition [J].

Shi, Jun ;

Li, Xiong-Jiang ;

Jiang, Shu-Yun ;

Wu, Wei ;

Ren, Hai .

ACS CATALYSIS, 2024, 14 (08) :5605-5611

[23] Copper-catalyzed oxidative C-H, N-H coupling of azoles and thiophenes [J].

Mitsuda, Shinobu ;

Fujiwara, Taiki ;

Kimigafukuro, Katsuyoshi ;

Monguchi, Daiki ;

Mori, Atsunori .

TETRAHEDRON, 2012, 68 (18) :3585-3590

[24] Site-selective remote C(sp3)-H heteroarylation of amides via organic photoredox catalysis [J].

Chen, Hui ;

Fan, Wenjing ;

Yuan, Xiang-Ai ;

Yu, Shouyun .

NATURE COMMUNICATIONS, 2019, 10 (1)

[25] Rhodium-catalyzed enantioselective in situ C(sp3 )-H heteroarylation by a desymmetrization approach [J].

Shi, Yujia ;

Qiao, Yan ;

Xie, Pengfei ;

Tian, Miaomiao ;

Li, Xingwei ;

Chang, Junbiao ;

Liu, Bingxian .

CHINESE CHEMICAL LETTERS, 2024, 35 (10)

[26] Copper-catalyzed direct monofluoroalkenylation of C(sp3)-H bonds via decarboxylation of α-fluoroacrylic acids [J].

Lu, Xiao-Yu ;

Chen, Xing-Ke ;

Gao, Meng-Ting ;

Sun, Xiao-Mei ;

Jiang, Run-Chuang ;

Wang, Jun-Chao ;

Yu, Li-Juan ;

Ge, Meng-Yuan ;

Wei, Zheng-Huan ;

Liu, Zi .

ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (17) :4712-4718

[27] Copper-Catalyzed Fluoroamide-Directed Remote C(sp3)-H Bond Functionalization Through Intramolecular Hydrogen Atom Transfer [J].

Lv, Xin ;

Yang, Yuhao ;

Zhou, Liejin ;

Zeng, Xiaojun .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (13)

[28] Fluorosulfonamide-Directed Heteroarylation of Aliphatic C(sp3)-H Bonds [J].

Pinter, Emily N. ;

Sheldon, Zachary S. ;

Modak, Atanu ;

Cook, Silas P. .

JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (07) :4757-4760

[29] Ligand-Free, Copper-Catalyzed Aerobic Benzylic sp3 C-H Oxygenation [J].

Tanaka, Hirotaka ;

Oisaki, Kounosuke ;

Kanai, Motomu .

SYNLETT, 2017, 28 (13) :1576-1580

[30] Copper-Catalyzed C(sp3)-C(sp3) Bond Formation Using a Hypervalent Iodine Reagent: An Efficient Allylic Trifluoromethylation [J].

Wang, Xi ;

Ye, Yuxuan ;

Zhang, Songnan ;

Feng, Jiajie ;

Xu, Yan ;

Zhang, Yan ;

Wang, Jianbo .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (41) :16410-16413

← 1 2 3 4 5 →