Sunlight-induced decarboxylative radical addition of carboxylic acids to electron-deficient alkenes using a millitube reactor

被引：7
|
作者：
Yoshimi, Yasuharu [1 ]
Nishio, Akinori [1 ]
Hayashi, Masae [1 ]
Morita, Toshio [1 ]
机构：
[1] Univ Fukui, Grad Sch Engn, Dept Appl Chem & Biotechnol, 3-9-1 Bunkyo, Fukui 9108507, Japan
来源：
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY | 2016年 / 331卷
关键词：
Sunlight-induced; Decarboxylative radical addition; Electron-deficient alkene; Millitube reactor; PHOTOCHEMICAL DECARBOXYLATION; 2+2 PHOTOCYCLOADDITION; PHOTOREDOX CATALYSIS; GREEN PHOTOCHEMISTRY; RING EXPANSION; COMPLEXES; ROUTE;
D O I：
10.1016/j.jphotochem.2016.03.012
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
The use of a fluorinated ethylene propylene (FEP) millitube reactor significantly improved the efficiency of the photoinduced decarboxylative radical addition of aliphatic carboxylic acids to electron-deficient alkenes, producing the corresponding gamma-amino acid derivative and macrocyclic lactone. These sunlight-induced photoreactions were achieved using a millitube reactor, even though the photosensitizer used in this system absorbs only UV light. (C) 2016 Elsevier B.V. All rights reserved.
引用
收藏
页码：17 / 21
页数：5
相关论文
共 31 条
  • [1] RADICAL-CHAIN ADDITION OF ARYLOXYL RADICALS TO ELECTRON-DEFICIENT ALKENES
    BAIK, W
    MIN, BC
    LEE, KC
    JUN, YM
    KIM, BH
    JOURNAL OF CHEMICAL RESEARCH-S, 1995, (09): : 366 - 367
  • [2] Efficient radical addition of tertiary amines to electron-deficient alkenes using semiconductors as photochemical sensitisers
    Marinkovic, S
    Hoffmann, N
    CHEMICAL COMMUNICATIONS, 2001, (17) : 1576 - 1577
  • [3] Decarbonylative radical conjugate addition of aliphatic aldehydes for alkylation of electron-deficient alkenes
    Li, Yu-Xia
    Li, Wei-Yu
    Jiang, Yuan-Yuan
    Yang, Luo
    TETRAHEDRON LETTERS, 2018, 59 (30) : 2934 - 2937
  • [4] Borohydride-Mediated Radical Addition Reactions of Organic Iodides to Electron-Deficient Alkenes
    Kawamoto, Takuji
    Uehara, Shohei
    Hirao, Hidefumi
    Fukuyama, Takahide
    Matsubara, Hiroshi
    Ryu, Ilhyong
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (09): : 3999 - 4007
  • [5] Acetal Addition to Electron-Deficient Alkenes with Hydrogen Atom Transfer as a Radical Chain Propagation Step
    Chan, Wei Chuen
    Vinod, Jincy K.
    Koide, Kazunori
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (04): : 3674 - 3682
  • [6] Radical α-addition involved electrooxidative [3+2] annulation of phenols and electron-deficient alkenes
    Zhao, Qiang
    Jin, Ji-Kang
    Wang, Jie
    Zhang, Feng-Lian
    Wang, Yi-Feng
    CHEMICAL SCIENCE, 2020, 11 (15) : 3909 - 3913
  • [7] Addition of a sulfur-stabilized radical to electron-deficient alkenes via phenyl selenide transfer
    Byers, JH
    Whitehead, CC
    Duff, ME
    TETRAHEDRON LETTERS, 1996, 37 (16) : 2743 - 2744
  • [8] Indium(III) acetate-catalyzed intermolecular radical addition of organic iodides to electron-deficient alkenes
    Miura, Katsukiyo
    Tomita, Mitsuru
    Ichikawa, Junji
    Hosomi, Akira
    ORGANIC LETTERS, 2008, 10 (01) : 133 - 136
  • [9] Visible-light photoredox catalyzed hydroacylation of electron-deficient alkenes: carboxylic anhydride as an acyl radical source
    Dong, Shupeng
    Wu, Guibing
    Yuan, Xiaoqian
    Zou, Chuncheng
    Ye, Jinxing
    ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (11): : 2230 - 2234
  • [10] Efficient Cu-catalyzed Atom Transfer Radical Addition Reactions of Fluoroalkylsulfonyl Chlorides with Electron-deficient Alkenes Induced by Visible Light
    Tang, Xiao-Jun
    Dolbier, William R., Jr.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (14) : 4246 - 4249
1234