Visible Light- and Heat-promoted C-O Coupling Reaction of Phenols and Aryl Halides

被引:26
作者
Yang, Qing-Qing [1 ]
Liu, Na [1 ]
Yan, Jia-Ping [1 ]
Ren, Zhi-Lin [2 ]
Wang, Long [1 ,3 ]
机构
[1] China Three Gorges Univ, Coll Mat & Chem Engn, Key Lab Inorgan Nonmetall Crystalline & Energy Co, Yichang 443002, Hubei, Peoples R China
[2] Hubei Univ Arts & Sci, Coll Chem Engn, Xiangyang 441053, Hubei, Peoples R China
[3] China Three Gorges Univ, Mat Anal & Testing Ctr, Yichang 443002, Hubei, Peoples R China
基金
中国国家自然科学基金;
关键词
visible light catalysis; electron donor-acceptor (EDA) complex; photocatalysts and ligands free; DFT calculation; C-O coupling; ONE-POT SYNTHESIS; PHOTOREDOX CATALYSIS; EFFICIENT SYNTHESIS; DIARYL ETHERS; PHOTOCHEMICAL ACTIVITY; MERGING PHOTOREDOX; REACTION STRATEGY; VINYL HALIDES; BOND; AMINATION;
D O I
10.1002/ajoc.201900666
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A visible light- and heat-promoted C-O coupling reaction of phenols and aryl halides has been described. Compared to the traditional C-O coupling reactions promoted by visible light, this strategy avoids the use of transition metals, photocatalysts and ligands. Moreover, the reaction has good substrate universality, suitable for substituted phenol, naphthol and heterocyclic phenol derivatives.
引用
收藏
页码:116 / 120
页数:5
相关论文
共 50 条
[21]   CuI Nanoparticles for C-N and C-O Cross Coupling of Heterocyclic Amines and Phenols with Chlorobenzenes [J].
Sreedhar, B. ;
Arundhathi, R. ;
Reddy, P. Linga ;
Kantam, M. Lakshmi .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (20) :7951-7954
[22]   Copper(II)-catalyzed C-O coupling of aryl bromides with aliphatic diols: synthesis of ethers, phenols, and benzo-fused cyclic ethers [J].
Liu, Yajun ;
Park, Se Kyung ;
Xiao, Yan ;
Chae, Junghyun .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (26) :4747-4753
[23]   Synthesis of chiral α-amino anilides via a DMEDA-promoted selective C-N coupling reaction of aryl halides and α-aminoamides [J].
Min, Xiangting ;
Li, Xiaoyu ;
Wang, Yu ;
Dong, Yawen ;
Tang, Jingjing ;
Wang, Jing ;
Liu, Jianhui .
TETRAHEDRON, 2018, 74 (21) :2561-2566
[24]   Light-driven C-O coupling of carboxylic acids and alkyl halides over a Ni single-atom catalyst [J].
Bajada, Mark A. ;
Di Liberto, Giovanni ;
Tosoni, Sergio ;
Ruta, Vincenzo ;
Mino, Lorenzo ;
Allasia, Nicolo ;
Sivo, Alessandra ;
Pacchioni, Gianfranco ;
Vile, Gianvito .
NATURE SYNTHESIS, 2023, 2 (11) :1092-1103
[25]   Discovery of a new palladacycle precatalyst and its applications to C-O coupling reactions between electron-deficient phenols and functionalized heteroaryl chlorides [J].
Zhang, Ting ;
Tudge, Matthew T. .
TETRAHEDRON LETTERS, 2015, 56 (18) :2329-2331
[26]   Cu2O Nanocube-Catalyzed Cross-Coupling of Aryl Halides with Phenols via Ullmann Coupling [J].
Kim, Jee Young ;
Park, Ji Chan ;
Kim, Aram ;
Kim, A. Young ;
Lee, Hyun Ju ;
Song, Hyunjoon ;
Park, Kang Hyun .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2009, (28) :4219-4223
[27]   Open air O-arylation reaction of phenols with aryl halides catalyzed by polymer-anchored copper(II) complexes [J].
Islam, Manirul ;
Mondal, Sanchita ;
Mondal, Paramita ;
Roy, Anupam Singha ;
Hossain, Dildar ;
Mobarak, Manir .
TRANSITION METAL CHEMISTRY, 2011, 36 (01) :1-11
[28]   CuSO4/N-(9H-carbazol-9-yl)picolinamide-Catalyzed C-O Coupling of (Hetero)Aryl Chlorides with Phenols on Water [J].
Hong, Peng ;
Zhu, Xinhai ;
Chen, Fu ;
Huang, Manna ;
Wan, Yiqian .
ORGANIC LETTERS, 2024, 26 (34) :7202-7206
[29]   Au(III)-aryl intermediates in oxidant-free C-N and C-O cross-coupling catalysis [J].
Serra, Jordi ;
Parella, Teodor ;
Ribas, Xavi .
CHEMICAL SCIENCE, 2017, 8 (02) :946-952
[30]   Visible light-promoted umpolung coupling of aryl tri-/difluoroethanones with 2-alkenylpyridines [J].
Xu, Xiao ;
Min, Qing-Qiang ;
Li, Na ;
Liu, Feng .
CHEMICAL COMMUNICATIONS, 2018, 54 (78) :11017-11020