Copper-Catalyzed Radical Bis(trifluoromethylation) of Alkynes and 1,3-Enynes

被引：32
|
作者：
Shen, Haigen [1 ,2 ]
Xiao, Hawen [1 ,2 ]
Zhu, Lin [1 ,2 ]
Li, Chaozhong [1 ,2 ,3 ]
机构：
[1] Chinese Acad Sci, Key Lab Organofluorine Chem, Shanghai Inst Organ Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China
[2] Chinese Acad Sci, Collaborat Innovat Ctr Chem Life Sci, Shanghai Inst Organ Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China
[3] Ningbo Univ Technol, Sch Mat & Chem Engn, 201 Fenghua Rd, Ningbo 315211, Zhejiang, Peoples R China
来源：
SYNLETT | 2020年 / 31卷 / 01期
基金：
上海市自然科学基金; 中国国家自然科学基金;
关键词：
copper; trifluoromethylation; radicals; alkynes; 1,3-enynes; SODIUM TRIFLUOROMETHANESULFINATE; SANDMEYER TRIFLUOROMETHYLATION; UNACTIVATED ALKENES; REAGENTS; IODIDES; FACILE;
D O I：
10.1055/s-0039-1690187
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The copper-catalyzed radical bis(trifluoromethylation) of alkynes and 1,3-enynes is described. With Cu(CH3CN)(4)BF4 as the catalyst, the reaction of arylalkynes with Togni reagent II and (bpy)Zn(CF3)(2) at room temperature affords the corresponding 1,2-bis(trifluoromethylated) alkenes in good yields with excellent E-stereoselectivity. Under similar conditions, the reaction of 1,3-enynes provides the corresponding 1,4-bis(trifluoromethylated) allenes exclusively in satisfactory yields. The protocol exhibits broad substrate scope and excellent functional group compatibility.
引用
收藏
页码：41 / 44
页数：4
相关论文
共 50 条
  • [21] Regio- and Stereoselective Copper-Catalyzed Borylation-Protodeboronation of 1,3-Diynes: Access to (Z)-1,3-Enynes
    Burgio, Ariel L.
    Buchbinder, Nicklas W.
    Santos, Webster L.
    ORGANIC LETTERS, 2023, 25 (15) : 2652 - 2656
  • [22] Photoinduced copper-catalyzed asymmetric radical three-component cross-coupling of 1,3-enynes with oxime esters and carboxylic acids
    Li, Guo-Qing
    Meng, Fan-Rong
    Xiao, Wen-Jing
    Chen, Jia-Rong
    ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (11) : 2773 - 2781
  • [23] Synthesis of trifluoromethylated allenes via visible light-promoted bis (trifluoromethylation) of 1,3-enynes
    Zhao, Yu-Rou
    Zhou, Yanchen
    Hu, Mingyou
    JOURNAL OF FLUORINE CHEMISTRY, 2023, 267
  • [24] Copper-Catalyzed Asymmetric 1,4-Aryl/Alkynylation of 1,3-Enynes to Access Axially Chiral Tetrasubstituted Allenes
    Huang, Han
    Zhang, Haiyan
    Wang, Qiaoling
    Sun, Youwen
    Su, Lei
    Xu, Wenru
    Ma, Yi
    Kong, Sheng
    Zhang, Guozhu
    Guo, Rui
    CHEMCATCHEM, 2023, 15 (16)
  • [25] Copper-Catalyzed Trifluoromethylation and Bicyclizations of 1,7-Enynes Leading to Fused Polycycles
    Wang, Qiang
    Song, Hongjian
    Liu, Yuxiu
    Song, Haibin
    Wang, Qingmin
    ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (21) : 3435 - 3442
  • [26] Ligand-accelerating low-loading copper-catalyzed effective synthesis of (E)-1,3-enynes by coupling between vinyl halides and alkynes performed in water
    Sun, Peng
    Yan, Hong
    Lu, Linhua
    Liu, Defu
    Rong, Guangwei
    Mao, Jincheng
    TETRAHEDRON, 2013, 69 (34) : 6969 - 6974
  • [27] Copper-Catalyzed One-Pot Synthesis of 1,3-Enynes from 2-Chloro-N-(quinolin-8-yl)acetamides and Terminal Alkynes
    Zhu, Lifan
    Guo, Hongyu
    Feng, Xiujuan
    Yamamoto, Yoshinori
    Bao, Ming
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (13): : 8740 - 8748
  • [28] Copper(I)-catalyzed asymmetric 1,3-dipolar cycloaddition of 1,3-enynes and azomethine ylides
    Wang, Bo-Ran
    Li, Yan-Bo
    Zhang, Qi
    Gao, Dingding
    Tian, Ping
    Li, Qinghua
    Yin, Liang
    NATURE COMMUNICATIONS, 2023, 14 (01)
  • [29] Copper(I)-catalyzed asymmetric 1,3-dipolar cycloaddition of 1,3-enynes and azomethine ylides
    Bo-Ran Wang
    Yan-Bo Li
    Qi Zhang
    Dingding Gao
    Ping Tian
    Qinghua Li
    Liang Yin
    Nature Communications, 14
  • [30] Transition metal-catalyzed couplings of alkynes to 1,3-enynes: modern methods and synthetic applications
    Trost, Barry M.
    Masters, James T.
    CHEMICAL SOCIETY REVIEWS, 2016, 45 (08) : 2212 - 2238
12345