Visible light-induced selective hydrobromodifluoromethylation of alkenes with dibromodifluoromethane

被引:75
作者
Lin, Qing-Yu [1 ]
Xu, Xiu-Hua [1 ]
Qing, Feng-Ling [1 ,2 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China
[2] Donghua Univ, Coll Chem Chem Engn & Biotechnol, Shanghai 201620, Peoples R China
基金
中国国家自然科学基金;
关键词
TRANSFER RADICAL-ADDITION; ETHYL 3-BROMO-3,3-DIFLUOROPROPIONATE; CATALYTIC HYDROTRIFLUOROMETHYLATION; TRIFLUOROMETHYLATION REACTIONS; ALPHA-TRIFLUOROMETHYLATION; STEREOSELECTIVE-SYNTHESIS; PHOTOREDOX; FLUORINE; EFFICIENT; BROMODIFLUOROMETHYLATION;
D O I
10.1039/c5ob01302j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A visible light-induced selective hydrobromodifluoromethylation of alkenes using CF2Br2 was developed. This transformation proceeded smoothly in the presence of catalytic eosin Y at room temperature to give various hydrobromodifluoromethylated compounds with broad functional group tolerance.
引用
收藏
页码:8740 / 8749
页数:10
相关论文
共 95 条
[81]   Visible-Light-Promoted Radical C-H Trifluoromethylation of Free Anilines [J].
Xie, Jin ;
Yuan, Xiangai ;
Abdukader, Ablimit ;
Zhu, Chengjian ;
Ma, Jing .
ORGANIC LETTERS, 2014, 16 (06) :1768-1771
[82]   Room temperature decarboxylative trifluoromethylation of α,β-unsaturated carboxylic acids by photoredox catalysis [J].
Xu, Pan ;
Abdukader, Ablimit ;
Hu, Kaidong ;
Cheng, Yixiang ;
Zhu, Chengjian .
CHEMICAL COMMUNICATIONS, 2014, 50 (18) :2308-2310
[83]   Synthetic Methods for Compounds Having CF3-S Units on Carbon by Trifluoromethylation, Trifluoromethylthiolation, Triflylation, and Related Reactions [J].
Xu, Xiu-Hua ;
Matsuzaki, Kohei ;
Shibata, Norio .
CHEMICAL REVIEWS, 2015, 115 (02) :731-764
[84]   Visible-Light Photoredox Catalysis [J].
Xuan, Jun ;
Xiao, Wen-Jing .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (28) :6828-6838
[85]   Boron-trihalide-promoted regioselective ring-opening reactions of gem-difluorocyclopropyl ketones [J].
Yang, Tang-Po ;
Li, Qiang ;
Lin, Jin-Hong ;
Xiao, Ji-Chang .
CHEMICAL COMMUNICATIONS, 2014, 50 (09) :1077-1079
[86]   Advances in Catalytic Enantioselective Fluorination, Mono-, Di-, and Trifluoromethylation, and Trifluoromethylthiolation Reactions [J].
Yang, Xiaoyu ;
Wu, Tao ;
Phipps, Robert J. ;
Toste, F. Dean .
CHEMICAL REVIEWS, 2015, 115 (02) :826-870
[87]   Intermolecular Aminotrifluoromethylation of Alkenes by Visible-Light-Driven Photoredox Catalysis [J].
Yasu, Yusuke ;
Koike, Takashi ;
Akita, Munetaka .
ORGANIC LETTERS, 2013, 15 (09) :2136-2139
[88]   Visible-light-induced synthesis of a variety of trifluoromethylated alkenes from potassium vinyltrifluoroborates by photoredox catalysis [J].
Yasu, Yusuke ;
Koike, Takashi ;
Akita, Munetaka .
CHEMICAL COMMUNICATIONS, 2013, 49 (20) :2037-2039
[89]   Three-component Oxytrifluoromethylation of Alkenes: Highly Efficient and Regioselective Difunctionalization of C=C Bonds Mediated by Photoredox Catalysts [J].
Yasu, Yusuke ;
Koike, Takashi ;
Akita, Munetaka .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (38) :9567-9571
[90]   Merging Visible-Light Photocatalysis and Transition-Metal Catalysis in the Copper-Catalyzed Trifluoromethylation of Boronic Acids with CF3I [J].
Ye, Yingda ;
Sanford, Melanie S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (22) :9034-9037