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

页数：10

共 50 条

[1] The construction of C(sp3)-O bond via copper porphyrin catalyzed cross-dehydrogenative coupling reaction: Substituent and electronic effect of the catalysts
Wang, Feng-Hua
Liu, Zheng-Yan
Yang, Shuang
Shi, Lei
Lin, Dong-Zi
Liu, Hai-Yang
Yuan, Gao-Qing
SYNTHETIC COMMUNICATIONS, 2021, 51 (13) : 2053 - 2062
[2] Iron porphyrin-catalyzed C(SP3) -H activation for the formation of C-O bond via cross-dehydrogenative coupling of cycloether and aromatic acid
Wen, Wei-Hong
Xie, An-Na
Wang, Hua-Hua
Zhang, Dong-Xu
Ali, Atif
Ying, Xiao
Liu, Hai-Yang
TETRAHEDRON, 2017, 73 (51) : 7169 - 7176
[3] Cross-dehydrogenative coupling for the intermolecular C-O bond formation
Krylov, Igor B.
Vil', Vera A.
Terent'ev, Alexander O.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2015, 11 : 92 - 146
[4] Merging Photoredox with Bronsted Acid Catalysis: The Cross-Dehydrogenative C-O Coupling for sp3 C-H Bond Peroxidation
Xia, Qing
Wang, Qiang
Yan, Changcun
Dong, Jianyang
Song, Hongjian
Li, Ling
Liu, Yuxiu
Wang, Qingmin
Liu, Xiangming
Song, Haibin
CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (45) : 10871 - 10877
[5] Copper porphyrin catalyzed esterification of C(sp3)-H via a cross-dehydrogenative coupling reaction
Wang, Hua-Hua
Wen, Wei-Hong
Zou, Huai-Bo
Cheng, Fan
Ali, Atif
Shi, Lei
Liu, Hai-Yang
Chang, Chi-Kwong
NEW JOURNAL OF CHEMISTRY, 2017, 41 (09) : 3508 - 3514
[6] Copper porphyrin-catalyzed C(sp2)-O bond construction via coupling phenols with formamides
Yang, Shuang
Chen, Xiao-Yan
Xiong, Ming-Feng
Zhang, Hao
Shi, Lei
Lin, Dong-Zi
Liu, Hai-Yang
JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2021, 68 (08) : 1541 - 1548
[7] Nanoporous gold catalyst for cross-dehydrogenative coupling via C-H bond activation
Ho, Hon Eong
Jin, Tienan
Asao, Naoki
Yamamoto, Yoshinori
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 246
[8] 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
[9] Cobalt(II)-Catalyzed Cross-Dehydrogenative Coupling Reaction of Benzamides with Alcohols to Build C-O Bond
Liu, Sheng-Kang
Cui, Xin-Feng
Liu, Xing-Xing
Ma, Hao-Jie
Wei, Dai-Dong
Luo, Xin-Liang
Huang, Guo-Sheng
CHEMISTRYSELECT, 2018, 3 (14): : 3989 - 3992
[10] Cu-catalyzed cross-dehydrogenative coupling:: A versatile strateav for C-C bond formations via the oxidative activation of sp3 C-H bonds
Li, Zhiping
Bohle, D. Scott
Li, Chao-Jun
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2006, 103 (24) : 8928 - 8933

← 1 2 3 4 5 →