Synthesis of Secondary Trifluoromethyl Boronic Esters through Visible Light Induced Decarboxylative Alkylation Reactions

被引:3
作者
Li, Weipiao [1 ,2 ]
Gao, Jiajun [1 ,2 ]
Mao, Ting [1 ,2 ]
Li, Xuefei [3 ]
Wang, An-Jun [2 ]
Wang, Pan [1 ]
Wang, Hao-Yang [2 ,4 ]
He, Chun-Yang [1 ,2 ]
机构
[1] Zunyi Med Univ, Affiliated Hosp Zunyi Med Univ, Dept Nucl Med, Zunyi 563000, Guizhou, Peoples R China
[2] Zunyi Med Univ, Gener Drug Res Ctr Guizhou Prov, Key Lab Biocatalysis & Chiral Drug Synth Guizhou P, Zunyi 563000, Guizhou, Peoples R China
[3] United Imaging Healthcare Grp Co Ltd, Cent Res Inst, Shanghai 201800, Peoples R China
[4] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
trifluoromethyl boronic esters; electron donor-acceptor complex; visible light induced; alkylation; QUATERNARY CARBONS; CONSTRUCTION; CF3;
D O I
10.1002/adsc.202300133
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
We demonstrated a practical and general methodology for the synthesis of secondary trifluoromethyl boronic esters through visible light induced decarboxylative alkylation reaction. This reaction was driven by the photochemical activity of electron donor-acceptor (EDA) complex. Except for wide group tolerance, moderate to high yields and simple reaction conditions, the practicality of this protocol was further demonstrated by direct modification of bioactive molecules and further derivations.
引用
收藏
页码:1596 / 1601
页数:6
相关论文
共 36 条
[21]   Metal-Free C(sp3)-H Allylation via Aryl Carboxyl Radicals Enabled by Donor-Acceptor Complex [J].
Li, Yang ;
Zhang, Jing ;
Li, Defang ;
Chen, Yiyun .
ORGANIC LETTERS, 2018, 20 (11) :3296-3299
[22]   Cu(II)-Catalyzed Enantioselective β-Boration of β-Trifluoromethyl, β,β-Disubstituted Enones and Esters: Construction of a CF3- and Boron-Containing Quaternary Stereocenter [J].
Liu, Bing ;
Wu, Hai-Hong ;
Zhang, Junliang .
ACS CATALYSIS, 2018, 8 (09) :8318-8323
[23]   Catalyst-Free and Visible Light Promoted Aminofluoroalkylation of Unactivated Alkenes: An Access to Fluorinated Aziridines [J].
Liu Xiao-Xiao ;
Jia Jia ;
Wang Ze ;
Zhang Yu-Ting ;
Chen Jiao ;
Yang Ke ;
He Chun-Yang ;
Zhao Liang .
ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (13) :2604-2608
[24]   18F-Trifluoromethylated D-Cysteine as a Promising New PET Tracer for Glioma Imaging: Comparative Analysis With MRI and Histopathology in Orthotopic C6 Models [J].
Ma, Hui ;
Zhao, Jing ;
Liu, Shaoyu ;
Xie, Dingxiang ;
Zhang, Zhanwen ;
Nie, Dahong ;
Wen, Fuhua ;
Yang, Zhiyun ;
Tang, Ganghua .
FRONTIERS IN ONCOLOGY, 2021, 11
[25]   Boron Neutron Capture Therapy: A Review of Clinical Applications [J].
Malouff, Timothy D. ;
Seneviratne, Danushka S. ;
Ebner, Daniel K. ;
Stross, William C. ;
Waddle, Mark R. ;
Trifiletti, Daniel M. ;
Krishnan, Sunil .
FRONTIERS IN ONCOLOGY, 2021, 11
[26]   A general and green fluoroalkylation reaction promoted via noncovalent interactions between acetone and fluoroalkyl iodides [J].
Mao, Ting ;
Ma, Ming-Jian ;
Zhao, Liang ;
Xue, De-Pu ;
Yu, Yanbo ;
Gu, Jiwei ;
He, Chun-Yang .
CHEMICAL COMMUNICATIONS, 2020, 56 (12) :1815-1818
[27]   N-(Acyloxy)phthalimides as Redox-Active Esters in Cross-Coupling Reactions [J].
Murarka, Sandip .
ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (09) :1735-1753
[28]   Ring-Opening Lithiation-Borylation of 2-Trifluoromethyl Oxirane: A Route to Versatile Tertiary Trifluoromethyl Boronic Esters [J].
Nandakumar, Meganathan ;
Rubial, Belen ;
Noble, Adam ;
Myers, Eddie L. ;
Aggarwal, Varinder K. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (03) :1187-1191
[29]   Single Electron Transfer-Induced Redox Processes Involving N-(Acyloxy)phthalimides [J].
Parida, Sushanta Kumar ;
Manda, Tanumoy ;
Das, Sanju ;
Hota, Sudhir Kumar ;
De Sarkar, Suman ;
Murarka, Sandip .
ACS CATALYSIS, 2021, 11 (03) :1640-1683
[30]   Limitations and Pitfalls of FDG-PET/CT in Infection and Inflammation [J].
Pijl, Jordy P. ;
Nienhuis, Pieter H. ;
Kwee, Thomas C. ;
Glaudemans, Andor W. J. M. ;
Slart, Riemer H. J. A. ;
Gormsen, Lars C. .
SEMINARS IN NUCLEAR MEDICINE, 2021, 51 (06) :633-645