CuSO4/N-(9H-carbazol-9-yl)picolinamide-Catalyzed C-O Coupling of (Hetero)Aryl Chlorides with Phenols on Water

被引:4
作者
Hong, Peng [1 ,2 ]
Zhu, Xinhai [2 ,3 ]
Chen, Fu [1 ]
Huang, Manna [1 ,2 ]
Wan, Yiqian [1 ,2 ]
机构
[1] Sun Yat Sen Univ, Sch Chem Engn & Technol, Zhuhai 519082, Peoples R China
[2] Sun Yat Sen Univ, Guangdong Engn Technol Res Ctr Platform Chem Marin, Zhuhai 519082, Peoples R China
[3] Sun Yat Sen Univ, Instrument Anal & Res Ctr, Guangzhou 510275, Peoples R China
基金
中国国家自然科学基金;
关键词
DIARYL ETHERS; ARYL HALIDES; CATALYZED ARYLATION; LIGAND; BOND; SUBSTITUTION;
D O I
10.1021/acs.orglett.4c02620
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A Cu-catalyzed C-O coupling of (hetero)aryl chlorides with phenols at 120 degrees C on water was developed with a designed ligand, N-(9H-carbazol-9-yl)picolinamide (L2). This method features a good substrate scope (both electron-donating and electron-withdrawing), low catalyst/ligand loadings (down to 1 mol %), and excellent scalability and practicability.
引用
收藏
页码:7202 / 7206
页数:5
相关论文
共 45 条
[1]   C(sp2)-O Bond Formation through a Nickel-Catalyzed Cross-Coupling Reaction in Water Enabled by Micellar Catalysis [J].
Ahanthem, Dini ;
Laitonjam, Warjeet S. .
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6 (10) :1492-1497
[2]   Novel electron-rich bulky phosphine ligands facilitate the palladium-catalyzed preparation of diaryl ethers [J].
Aranyos, A ;
Old, DW ;
Kiyomori, A ;
Wolfe, JP ;
Sadighi, JP ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (18) :4369-4378
[3]   Exploration of Nitroaromatic Antibiotics via Sanger's Reagent: Synthesis, In Silico, and Antimicrobial Evaluation [J].
Ayoup, Mohammed Salah ;
Rabee, Ahmed R. ;
Abdel-Hamid, Hamida ;
Harras, Marwa F. ;
El Menofy, Nagwan G. ;
Ismail, Magda M. F. .
ACS OMEGA, 2022, 7 (06) :5254-5263
[4]   Pd/PTABS: Low Temperature Etherification of Chloroheteroarenes [J].
Bhilare, Shatrughn ;
Bandaru, Siva Sankar Murthy ;
Shah, Jagrut ;
Chrysochos, Nicolas ;
Schulzke, Carola ;
Sanghvi, Yogesh S. ;
Kapdi, Anant R. .
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (21) :13088-13102
[5]   Selected Copper-Based Reactions for C-N, C-O, C-S, and C-C Bond Formation [J].
Bhunia, Subhajit ;
Pawar, Govind Goroba ;
Kumar, S. Vijay ;
Jiang, Yongwen ;
Ma, Dawei .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (51) :16136-16179
[6]  
Bullock R. M., 2010, CATALYSIS WITHOUTPRE, DOI [10.1002/cctc.201000430, DOI 10.1002/CCTC.201000430]
[7]   Significantly improved method for the Pd-catalyzed coupling of phenols with aryl halides: Understanding ligand effects [J].
Burgos, Carlos H. ;
Barder, Timothy E. ;
Huang, Xiaohua ;
Buchwald, Stephen L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (26) :4321-4326
[8]   A Review on the Latest Progress of Chan-Lam Coupling Reaction [J].
Chen, Jin-Quan ;
Li, Jing-Hang ;
Dong, Zhi-Bing .
ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (16) :3311-3331
[9]   Water as the reaction medium in organic chemistry: from our worst enemy to our best friend [J].
Cortes-Clerget, Margery ;
Yu, Julie ;
Kincaid, Joseph R. A. ;
Walde, Peter ;
Gallou, Fabrice ;
Lipshutz, Bruce H. .
CHEMICAL SCIENCE, 2021, 12 (12) :4237-4266
[10]   Room-Temperature Cul-Catalyzed Amination of Aryl Iodides and Aryl Bromides [J].
Ding, Xiaomei ;
Huang, Manna ;
Yi, Zhou ;
Du, Dongchen ;
Zhu, Xinhai ;
Wan, Yiqian .
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (10) :5416-5423