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
[21]   DIFLUOROMETHYLATION OF ALKENES VIA BOROHYDRIDE REDUCTION OF 1,3-DIBROMO-1,1-DIFLUOROALKANES [J].
GONZALEZ, J ;
FOTI, CJ ;
ELSHEIMER, S .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (13) :4322-4325
[22]   Oxidant-induced addition reaction of perfluoroalkyl halides to alkenes and alkynes [J].
Guo, XC ;
Chen, QY .
JOURNAL OF FLUORINE CHEMISTRY, 1998, 88 (01) :63-70
[23]   Selective defluorination approach to N-cbz-3,3-difluoro-2-difluoromethylenepyrrolidine and its application to 3,3-difluoroproline dipeptide synthesis [J].
Guo, Yong ;
Fujiwara, Kana ;
Amii, Hideki ;
Uneyama, Kenji .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (22) :8523-8526
[24]   The many roles for fluorine in medicinal chemistry [J].
Hagmann, William K. .
JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (15) :4359-4369
[25]   Synthetic applications of eosin Y in photoredox catalysis [J].
Hari, Durga Prasad ;
Koenig, Burkhard .
CHEMICAL COMMUNICATIONS, 2014, 50 (51) :6688-6699
[26]   Synthesis of mono- and difluoroacetyltrialkylsilanes and the corresponding enol silyl ethers [J].
Higashiya, S ;
Chung, WJ ;
Lim, DS ;
Ngo, SC ;
Kelly, WH ;
Toscano, PJ ;
Welch, JT .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (19) :6323-6328
[28]   A CONVENIENT SYNTHESIS OF BROMODIFLUOROMETHYL-SUBSTITUTED ALKENES [J].
HU, CM ;
CHEN, J .
JOURNAL OF FLUORINE CHEMISTRY, 1994, 69 (01) :79-84
[29]   Sodium dithionite initiated addition of CF2Br2, CF3I and (CF3)2CFI to allylaromatics.: Synthesis and the reactivity of 4-aryl-1,1-difluorodienes and 4-aryl-1,1-bis(trifluoromethyl)dienes [J].
Ignatowska, Jolanta ;
Dmowski, Wojciech .
JOURNAL OF FLUORINE CHEMISTRY, 2007, 128 (09) :997-1006
[30]   Controlled Trifluoromethylation Reactions of Alkynes through Visible-Light Photoredox Catalysis [J].
Iqbal, Naeem ;
Jung, Jaehun ;
Park, Sehyun ;
Cho, Eun Jin .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (02) :539-542