s-Tetrazine-functionalized hyper-crosslinked polymers for efficient photocatalytic synthesis of benzimidazoles

被引:55
作者
An, Wan-Kai [1 ]
Zheng, Shi-Jia [1 ]
Zhang, Hui-Xing [1 ]
Shang, Tian-Tian [1 ]
Wang, He-Rui [2 ]
Xu, Xiao-Jing [1 ]
Jin, Qiu [1 ]
Qin, Yuchen [1 ]
Ren, Yunlai [1 ]
Jiang, Song [1 ]
Xu, Cui-Lian [1 ]
Hou, Mao-Song [1 ]
Pan, Zhenliang [1 ]
机构
[1] Henan Agr Univ, Coll Sci, Zhengzhou 450002, Hennan, Peoples R China
[2] Henan Agr Univ, Coll Food Sci & Technol, Zhengzhou 450002, Hennan, Peoples R China
基金
中国国家自然科学基金;
关键词
POROUS ORGANIC POLYMERS; CONJUGATED MICROPOROUS POLYMERS; PERIODIC MESOPOROUS ORGANOSILICAS; ONE-POT SYNTHESIS; HETEROGENEOUS CATALYSTS; 3,6-DI(PYRIDIN-2-YL)-1,2,4,5-TETRAZINE PYTZ; HYPERCROSSLINKED POLYMERS; GREEN SYNTHESIS; FRAMEWORKS; OXIDATION;
D O I
10.1039/d0gc03719b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Developing green-safe, efficient and recyclable catalysts is crucial for the chemical industry. So far, organic photocatalysis has been proved to be an environmentally friendly and energy-efficient synthetic technology compared with traditional metal catalysis. As a versatile catalytic platform, hyper-crosslinked polymers (HCPs) with large surface area and high stability are easily prepared. In this report, we successfully constructed two porous HCP photocatalysts (TZ-HCPs) featuring s-tetrazine units and surface areas larger than 700 m(2) g(-1) through Friedel-Crafts alkylation reactions. The rational energy-band structures and coexisting micro- and mesopores endow TZ-HCPs with excellent activities to realize the green synthesis of benzimidazoles (28 examples, up to 99% yield, 0.5-4.0 h) in ethanol. Furthermore, at least 21 iterative catalytic runs mediated by TZ-HCP1D were performed efficiently, with 96-99% yield. This study of TZ-HCPs sheds light on the wide-ranging prospects of application of HCPs as metal-free and green photocatalysts for the preparation of fine chemicals.
引用
收藏
页码:1292 / 1299
页数:8
相关论文
共 95 条
[1]   Thiophene-embedded conjugated microporous polymers for photocatalysis [J].
An, Wan-Kai ;
Zheng, Shi-Jia ;
Du, Ya-Nan ;
Ding, San-Yuan ;
Li, Zhi-Jun ;
Jiang, Song ;
Qin, Yuchen ;
Liu, Xiaobiao ;
Wei, Pi-Feng ;
Cao, Zhan-Qi ;
Song, Meirong ;
Pan, Zhenliang .
CATALYSIS SCIENCE & TECHNOLOGY, 2020, 10 (15) :5171-5180
[2]   Designing conjugated microporous polymers for visible light-promoted photocatalytic carbon-carbon double bond cleavage in aqueous medium [J].
Ayed, Cyrine ;
da Silva, Lucas Caire ;
Wang, Di ;
Zhang, Kai A. I. .
JOURNAL OF MATERIALS CHEMISTRY A, 2018, 6 (44) :22145-22151
[3]   tert-Butyl nitrite catalyzed synthesis of benzimidazoles from o-phenylenediamine and aldehydes at room temperature [J].
Azeez, Sadaf ;
Sureshbabu, Popuri ;
Chaudhary, Priyanka ;
Sabiah, Shahulhameed ;
Kandasamy, Jeyakumar .
TETRAHEDRON LETTERS, 2020, 61 (14)
[4]   Synthesis of benzimidazoles and benzoxazoles using TiCl3OTf in ethanol at room temperature [J].
Azizian, Javad ;
Torabi, Parviz ;
Noei, Jalil .
TETRAHEDRON LETTERS, 2016, 57 (02) :185-188
[5]   Mild and highly efficient method for the synthesis of 2-arylbenzimidazoles and 2-arylbenzothiazoles [J].
Bahrami, Kiumars ;
Khodaei, M. Mehdi ;
Naali, Fardin .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (17) :6835-6837
[6]   Metal-Organic Frameworks in Heterogeneous Catalysis: Recent Progress, New Trends, and Future Perspectives [J].
Bavykina, Anastasiya ;
Kolobov, Nikita ;
Khan, Il Son ;
Bau, Jeremy A. ;
Ramirez, Adrian ;
Gascon, Jorge .
CHEMICAL REVIEWS, 2020, 120 (16) :8468-8535
[7]   Molecular artificial photosynthesis [J].
Berardi, Serena ;
Drouet, Samuel ;
Francas, Laia ;
Gimbert-Surinach, Carolina ;
Guttentag, Miguel ;
Richmond, Craig ;
Stoll, Thibaut ;
Llobet, Antoni .
CHEMICAL SOCIETY REVIEWS, 2014, 43 (22) :7501-7519
[8]   Functionalized periodic mesoporous organosilicas: from metal free catalysis to sensing [J].
Bourda, Laurens ;
Jena, Himanshu Sekhar ;
Van Deun, Rik ;
Kaczmarek, Anna M. ;
Van der Voort, Pascal .
JOURNAL OF MATERIALS CHEMISTRY A, 2019, 7 (23) :14060-14069
[9]   Hybrid micro-/nano-structures derived from metal-organic frameworks: preparation and applications in energy storage and conversion [J].
Cao, Xiehong ;
Tan, Chaoliang ;
Sindoro, Melinda ;
Zhang, Hua .
CHEMICAL SOCIETY REVIEWS, 2017, 46 (10) :2660-2677
[10]   Cooperative iridium complex-catalyzed synthesis of quinoxalines, benzimidazoles and quinazolines in water [J].
Chakrabarti, Kaushik ;
Maji, Milan ;
Kundu, Sabuj .
GREEN CHEMISTRY, 2019, 21 (08) :1999-2004