Recent Progress in Visible-Light Photoredox-Catalyzed Intermolecular 1,2-Difunctionalization of Double Bonds via an ATRA-Type Mechanism

被引：265
作者：
Courant, Thibaut [1 ]
Masson, Geraldine [1 ]
机构：
[1] Univ Paris Saclay, Univ Paris 11, Inst Chim Subst Nat, CNRS UPR 2301, F-91198 Gif Sur Yvette, France
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 16期
关键词：
TRANSFER RADICAL-ADDITION; CONCOMITANT INTRODUCTION; COMBINING PHOTOREDOX; PSCHORR REACTION; FACILE SYNTHESIS; DIAZONIUM SALTS; TRIFLUOROMETHYLATION; ALKENES; EFFICIENT; PHOTOCATALYSIS;
D O I：
10.1021/acs.joc.6b01058
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Radical difunctionalizations of alkenes constitute an efficient method for the construction of complex organic molecules. This synopsis focuses on visible-light catalysis, a recent and very promising technological refinement of this class of transformations. Examples taken from the literature illustrate the use of a variety of (metallic or nonmetallic) systems, which allow us to leverage the energy of readily available visible-light radiation to efficiently create some of the most commonly rooked for types of bonds (C-X, C-O, C-N, and C-C) under mild conditions and starting from unsaturated substrates.
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收藏
页码：6945 / 6952
页数：8
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共 79 条
  • [1] 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
  • [2] Oxydifluoromethylation of Alkenes by Photoredox Catalysis: Simple Synthesis of CF2H-Containing Alcohols
    Arai, Yusuke
    Tomita, Ren
    Ando, Gaku
    Koike, Takashi
    Akita, Munetaka
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (04) : 1262 - 1265
  • [3] Photo-Organocatalysis of Atom-Transfer Radical Additions to Alkenes
    Arceo, Elena
    Montroni, Elisa
    Melchiorre, Paolo
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (45) : 12064 - 12068
  • [4] Trifluoromethylchlorosulfonylation of Alkenes: Evidence for an Inner-Sphere Mechanism by a Copper Phenanthroline Photoredox Catalyst
    Bagal, Dattatraya B.
    Kachkovskyi, Georgiy
    Knorn, Matthias
    Rawner, Thomas
    Bhanage, Bhalchandra M.
    Reiser, Oliver
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (24) : 6999 - 7002
  • [5] Photocatalytic fluoroalkylation reactions of organic compounds
    Barata-Vallejo, Sebastian
    Bonesi, Sergio M.
    Postigo, Al
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (46) : 11153 - 11183
  • [6] RU(BPY)(3)(2+)-MEDIATED ADDITION OF SE-PHENYL P-TOLUENESELENOSULFONATE TO ELECTRON-RICH OLEFINS
    BARTON, DHR
    CSIBA, MA
    JASZBERENYI, JC
    [J]. TETRAHEDRON LETTERS, 1994, 35 (18) : 2869 - 2872
  • [7] PHOTOCATALYSIS OF THE PSCHORR REACTION BY TRIS-(2,2'-BIPYRIDYL)RUTHENIUM(II) IN THE PHENANTHRENE SERIES
    CANOYELO, H
    DERONZIER, A
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1984, (06): : 1093 - 1098
  • [8] PHOTO-OXIDATION OF SOME CARBINOLS BY THE RU(II) POLYPYRIDYL COMPLEX ARYL DIAZONIUM SALT SYSTEM
    CANOYELO, H
    DERONZIER, A
    [J]. TETRAHEDRON LETTERS, 1984, 25 (48) : 5517 - 5520
  • [9] PHOTO-OXIDATION OF TRIS(2,2'-BIPYRIDINE)RUTHENIUM(II) BY PARA-SUBSTITUTED BENZENE DIAZONIUM SALTS IN ACETONITRILE 2-COMPARTMENT PHOTOELECTROCHEMICAL CELL APPLICATIONS
    CANOYELO, H
    DERONZIER, A
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-FARADAY TRANSACTIONS I, 1984, 80 : 3011 - 3019
  • [10] PHOTOCATALYSIS OF THE PSCHORR REACTION BY RU(BPY)32+ IN THE FLUORENONE, FLUORENE AND DIBENZOFURAN SERIES
    CANOYELO, H
    DERONZIER, A
    [J]. JOURNAL OF PHOTOCHEMISTRY, 1987, 37 (02): : 315 - 321
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