Construction of C-O bond via cross-dehydrogenative coupling of sp [3] C-H bond with phenols catalyzed by copper porphyrin

被引：8
|
作者：
Yang, Shuang [1 ]
Xiong, Ming-Feng [1 ]
Tian, Wan-Qun [1 ]
Zhang, Hao [1 ]
Xiao, Xin-Yan [1 ]
Liu, Hai-Yang [1 ]
Chang, Chi-Kwong [2 ]
机构：
[1] South China Univ Technol, Dept Chem, Key Lab Funct Mol Engn Guangdong Prov, Guangzhou 510641, Peoples R China
[2] Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA
来源：
TETRAHEDRON | 2020年 / 76卷 / 45期
基金：
中国国家自然科学基金;
关键词：
Cross-dehydrogenative coupling; Phenolic etherification; Porphyrin; Copper; ACTIVATION; ESTERIFICATION; FORMAMIDES; MECHANISM; ETHERS; C(SP(3))-H; RADICALS;
D O I：
10.1016/j.tet.2020.131569
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Copper porphyrin-catalyzed construction of ether bond by cross-dehydrogenative coupling of sp [3] C-H bond with phenols bearing electron-withdrawing groups (EWG) was described for the first time. A broad range of substrates afforded different acetals in moderate to excellent yields with good functional group tolerance. The developed method is not only suitable for phenol substrates with ortho-directing groups, but also suitable for those phenol without ortho-directing groups. Significantly, a high turnover number (TON) up to 7300 was achieved in gram-level test. (C) 2020 Elsevier Ltd. All rights reserved.
引用
收藏
页数：10
相关论文
共 50 条
  • [31] On Inventing Cross-Dehydrogenative Coupling (CDC): Forming C-C Bond from Two Different C-H Bonds
    Li, Chao-Jun
    CHINESE JOURNAL OF CHEMISTRY, 2022, 40 (07) : 838 - 845
  • [32] Copper-catalyzed arene C-H bond cross-coupling
    Do, Hien-Quang
    Daugulis, Olafs
    CHEMICAL COMMUNICATIONS, 2009, (42) : 6433 - 6435
  • [33] Cross-dehydrogenative coupling: a sustainable reaction for C-C bond formations
    Tian, Tian
    Li, Zhiping
    Li, Chao-Jun
    GREEN CHEMISTRY, 2021, 23 (18) : 6789 - 6862
  • [34] An unprecedented tandem synthesis of fluorescent coumarin-fused pyrimidines via copper-catalyzed cross-dehydrogenative C(sp3)-N bond coupling
    Kumari, Santosh
    Shakoor, S. M. Abdul
    Khullar, Sadhika
    Mandal, Sanjay K.
    Sakhuja, Rajeev
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (17) : 3220 - 3228
  • [35] Expedient Ni-catalyzed C-H/C-H cross-dehydrogenative coupling of aryl amides with azoles
    Sarkar, Tanumay
    Maharana, Prabhat Kumar
    Roy, Subhasish
    Punniyamurthy, Tharmalingam
    CHEMICAL COMMUNICATIONS, 2022, 58 (40) : 5980 - 5983
  • [36] Copper catalyzed C-O bond formation by direct C-H activation of THF with phenols: an approach to the synthesis of phenyl tetrahydrofuranyl ethers
    Vala, Manoj Kumar
    Adurthi, Suryakumari
    Chithaluri, Sudhakar
    SYNTHETIC COMMUNICATIONS, 2021, 51 (06) : 913 - 920
  • [37] Formation of C-O Bond via Cross-Dehydrogenative Coupling between Isochroman and Oxime under Metal-Free Oxidation Conditions
    He, Hua-Feng
    Wang, Kai
    Xing, Bo
    Sheng, Guorong
    Ma, Tingxuan
    Bao, Weiliang
    SYNLETT, 2013, 24 (02) : 211 - 214
  • [38] Recent Advances in Cross-Dehydrogenative Couplings (CDC) of C-H Bond in Aqueous Media
    Peng, Kang
    Dong, Zhi-Bing
    ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (05) : 1185 - 1201
  • [39] Photochemical C-H bond coupling for (hetero)aryl C(sp2)-C(sp3) bond construction
    Zhao, Yating
    Xia, Wujiong
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (20) : 4951 - 4963
  • [40] 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
12345