Visible Light Catalyzed Reductive Cross-Coupling of α-CF3-alkyl Bromide and Alkynyl Bromide

被引:4
作者
Tian, Yiqiang [1 ]
Li, Yi [1 ]
Zhang, Chun [1 ]
机构
[1] Tianjin Univ, Inst Mol Plus, Fac Med, Sch Pharmaceut Sci & Technol,Dept Chem, 92 Weijin Rd, Tianjin 300072, Peoples R China
基金
中国国家自然科学基金;
关键词
Visiable light catalysis; C-C bond formation; Reductive cross-coupling; Trifluoromethyl group; Alkynyl group; Radicals; Organohalides; Photochemistry; AMINOALKYL RADICALS; TRIFLUOROMETHYLATION; ELECTROPHILES; DERIVATIVES; ACTIVATION; ACIDS;
D O I
10.1002/cjoc.202400402
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Traditional reduction coupling reactions of two bromides typically rely on transition metal catalysis. Here, we introduce the development of a visible-light catalytic direct reduction coupling reaction between alpha-CF3-alkyl bromides and alkynyl bromides to access valuable organic frameworks. Our research confirms the excellent compatibility of this reaction with various functional groups, which could be used to modify the substrate with biologically active molecular fragments. Mechanistic investigations, including control experiments, fluorescence quenching studies, and light-switching experiments, have provided insights into the reaction mechanism. This study paves the way for the application of visible-light catalysis in diverse synthetic transformations, offering a sustainable and efficient approach to organic synthesis.
引用
收藏
页码:2479 / 2484
页数:6
相关论文
共 66 条
[1]   Aryl Transfer Strategies Mediated by Photoinduced Electron Transfer [J].
Allen, Anthony R. ;
Noten, Efrey A. ;
Stephenson, Corey R. J. .
CHEMICAL REVIEWS, 2022, 122 (02) :2695-2751
[2]   Carbon Trifluoromethylation Reactions of Hydrocarbon Derivatives and Heteroarenes [J].
Alonso, Concepcion ;
Martinez de Marigorta, Eduardo ;
Rubiales, Gloria ;
Palacios, Francisco .
CHEMICAL REVIEWS, 2015, 115 (04) :1847-1935
[3]   Palladium-Catalyzed Direct Ethynylation of C(sp3)-H Bonds in Aliphatic Carboxylic Acid Derivatives [J].
Ano, Yusuke ;
Tobisu, Mamoru ;
Chatani, Naoto .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (33) :12984-12986
[4]   Aminoalkyl Radicals as Powerful Intermediates for the Synthesis of Unnatural Amino Acids and Peptides [J].
Aycock, R. Adam ;
Pratt, Cameron J. ;
Jui, Nathan T. .
ACS CATALYSIS, 2018, 8 (10) :9115-9119
[5]   Kinetic Isotope Effects in Reductive Excited-State Quenching of Ru(2,2′-bipyrazine)32+ by Phenols [J].
Bronner, Catherine ;
Wenger, Oliver S. .
JOURNAL OF PHYSICAL CHEMISTRY LETTERS, 2012, 3 (01) :70-74
[6]   Metallaphotoredox: The Merger of Photoredox and Transition Metal Catalysis [J].
Chan, Amy Y. ;
Perry, Ian B. ;
Bissonnette, Noah B. ;
Buksh, Benito F. ;
Edwards, Grant A. ;
Frye, Lucas, I ;
Garry, Olivia L. ;
Lavagnino, Marissa N. ;
Li, Beryl X. ;
Liang, Yufan ;
Mao, Edna ;
Millet, Agustin ;
Oakley, James, V ;
Reed, Nicholas L. ;
Sakai, Holt A. ;
Seath, Ciaran P. ;
MacMillan, David W. C. .
CHEMICAL REVIEWS, 2022, 122 (02) :1485-1542
[7]   Visible light photoredox-controlled reactions of N-radicals and radical ions [J].
Chen, Jia-Rong ;
Hu, Xiao-Qiang ;
Lu, Liang-Qiu ;
Xiao, Wen-Jing .
CHEMICAL SOCIETY REVIEWS, 2016, 45 (08) :2044-2056
[8]   LiBr-Mediated Cross-Coupling towards α-Trifluoromethylamines [J].
Chen, Yongzhi ;
Lin, Dengkai ;
Yu, Zijie ;
Dong, Zhan ;
Song, Liangliang ;
Chen, Liang-An .
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 12 (08)
[9]   Nickel-Catalyzed Carbonylation of Secondary Trifluoromethylated, Difluoromethylated, and Nonfluorinated Aliphatic Electrophiles with Arylboronic Acids under 1 atm of CO [J].
Cheng, Ran ;
Zhao, Hai-Yang ;
Zhang, Shu ;
Zhang, Xingang .
ACS CATALYSIS, 2020, 10 (01) :36-42
[10]   Visible-Light-Induced Photoredox 1,1-Dichloromethylation of Alkenes with Chloroform [J].
Cheng, Yingjie ;
Qu, Zhonghua ;
Chen, Shiru ;
Ji, Xiaochen ;
Deng, Guo-Jun ;
Huang, Huawen .
ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (09) :1573-1579