Photoredox relay-catalyzed gem-difluoroallylation of alkyl iodides

被引:27
作者
Guo, Yuanqiang [1 ]
Cao, Yunpeng [1 ]
Song, Hongjian [1 ]
Liu, Yuxiu [1 ]
Wang, Qingmin [1 ]
机构
[1] Nankai Univ, Coll Chem, Frontiers Sci Ctr New Organ Matter, Res Inst Elementoorgan Chem,State Key Lab Element, Tianjin 300071, Peoples R China
基金
中国国家自然科学基金;
关键词
C-F; BIOLOGICAL-ACTIVITY; DIAZO-COMPOUNDS; DIFLUOROALKENES; TRIFLUOROMETHYLATION; DIFLUOROOLEFINATION; DIFLUOROCARBENE; DERIVATIVES; ACID;
D O I
10.1039/d1cc04284j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Herein, a new example of relay catalysis, using a combination of Mn-2(CO)(10) and an iridium-based photocatalyst, is reported. In our relay catalytic reaction, the Mn catalyst and iridium-based photocatalyst catalyze the reaction at different stages in the desired sequence under the same reaction conditions, and do not inhibit each other. This convenient method transforms a broad scope of alkyl iodides into the corresponding gem-difluoroalkenes via C(sp(3))-C(sp(3)) bond construction. The protocol has good functional group tolerance and is suitable for the late-stage modification of multifunctional complex molecules.
引用
收藏
页码:9768 / 9771
页数:4
相关论文
共 53 条
  • [1] Development of (Trifluoromethyl)zinc Reagent as Trifluoromethyl Anion and Difluorocarbene Sources
    Aikawa, Kohsuke
    Toya, Wataru
    Nakamura, Yuzo
    Mikami, Koichi
    [J]. ORGANIC LETTERS, 2015, 17 (20) : 4996 - 4999
  • [2] Carbon Trifluoromethylation Reactions of Hydrocarbon Derivatives and Heteroarenes
    Alonso, Concepcion
    Martinez de Marigorta, Eduardo
    Rubiales, Gloria
    Palacios, Francisco
    [J]. CHEMICAL REVIEWS, 2015, 115 (04) : 1847 - 1935
  • [3] SYNTHESIS AND BIOLOGICAL-ACTIVITY OF 5-(2,2-DIFLUOROVINYL)-2'-DEOXYURIDINE
    BOBEK, M
    KAVAI, I
    DECLERCQ, E
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (08) : 1494 - 1497
  • [4] Synthesis and Metal-Catalyzed Reactions of gem-Dihalovinyl Systems
    Chelucci, Giorgio
    [J]. CHEMICAL REVIEWS, 2012, 112 (03) : 1344 - 1462
  • [5] Visible-Light-Induced Radical Defluoroborylation of Trifluoromethyl Alkenes: An Access to gem-Difluoroallylboranes
    Chen, Guojun
    Wang, Liling
    Liu, Xiaozu
    Liu, Peijun
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (14) : 2990 - 2996
  • [6] Synthesis of gem-Difluoroalkenes via Zn-Mediated Decarboxylative/Defluorinative Cross-Coupling
    Du, Hai-Wu
    Chen, Yang
    Sun, Jing
    Gao, Qi-Sheng
    Wang, He
    Zhou, Ming-Dong
    [J]. ORGANIC LETTERS, 2020, 22 (23) : 9342 - 9345
  • [7] 9-ALPHA-FLUORO DERIVATIVES OF CORTISONE AND HYDROCORTISONE
    FRIED, J
    SABO, EF
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (05) : 1455 - 1456
  • [8] Substitution of Two Fluorine Atoms in a Trifluoromethyl Group: Regioselective Synthesis of 3-Fluoropyrazoles
    Fuchibe, Kohei
    Takahashi, Masaki
    Ichikawa, Junji
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (48) : 12059 - 12062
  • [9] Transition-Metal-Mediated and -Catalyzed C-F Bond Activation by Fluorine Elimination
    Fujita, Takeshi
    Fuchibe, Kohei
    Ichikawa, Junji
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (02) : 390 - 402
  • [10] Difluoromethyl 2-pyridyl sulfone: a versatile carbonyl gem-difluoroolefination reagent
    Gao, Bing
    Zhao, Yanchuan
    Hu, Jingyu
    Hu, Jinbo
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (02): : 163 - 168