Acyl Radicals from Acylsilanes: Photoredox-Catalyzed Synthesis of Unsymmetrical Ketones

被引：108
作者：
Capaldo, Luca [1 ]
Riccardi, Riccardo [1 ]
RaveIli, Davide [1 ]
Fagnoni, Maurizio [1 ]
机构：
[1] Univ Pavia, Dept Chem, PhotoGreen Lab, Viale Taramelli 12, I-27100 Pavia, Italy
来源：
ACS CATALYSIS | 2018年 / 8卷 / 01期
关键词：
photoredox catalysis; acylsilanes; acyl radicals; decatungstate salts; acridinium salts; VISIBLE-LIGHT PHOTOCATALYSIS; C-H; MECHANISTIC PHOTOCHEMISTRY; ELECTROCHEMICAL OXIDATION; DIALKYL AZODICARBOXYLATES; ELECTROPHILIC OLEFINS; DECATUNGSTATE ANION; MERGING PHOTOREDOX; SILA-STETTER; ACYLATION;
D O I：
10.1021/acscatal.7b03719
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：
Acyl radicals were smoothly generated from acylsilanes under photoredox-catalyzed conditions. These radicals were formed upon ultraviolet B (UV-B), solar, or visible light irradiation by using decatungstate and acridinium salts as photocatalysts. Acylation of Michael acceptors and a few styrenes resulted in a smooth preparation of unsymmetrical ketones in yields up to 89%.
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页码：304 / 309
页数：6
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共 85 条
  • [1] Toward a mild dehydroformylation using base-metal catalysis
    Abrams, Dylan J.
    West, Julian G.
    Sorensen, Erik J.
    [J]. CHEMICAL SCIENCE, 2017, 8 (03) : 1954 - 1959
  • [2] Formation of 2-Cyano-2-siloxyvinylallenes via Cyanide-Induced Brook Rearrangement in γ-Bromo-α,β,γ,δ-unsaturated Acylsilanes
    Ando, Masafumi
    Sasaki, Michiko
    Miyashita, Izumi
    Takeda, Kei
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (01) : 247 - 255
  • [3] Acylsilanes in Iridium-Catalyzed Directed Amidation Reactions and Formation of Heterocycles via Siloxycarbenes
    Becker, Peter
    Pirwerdjan, Ramona
    Bolm, Carsten
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (51) : 15493 - 15496
  • [4] Acylsilanes in Rhodium(III)-Catalyzed Directed Aromatic C-H Alkenylations and Siloxycarbene Reactions with C-C Double Bonds
    Becker, Peter
    Priebbenow, Daniel L.
    Pirwerdjan, Ramona
    Bolm, Carsten
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (01) : 269 - 271
  • [5] Visible-Light-Mediated Photocatalytic Difunctionalization of Olefins by Radical Acylarylation and Tandem Acylation/Semipinacol Rearrangement
    Bergonzini, Giulia
    Cassani, Carlo
    Lorimer-Olsson, Haldor
    Horberg, Johanna
    Wallentin, Carl-Johan
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (10) : 3292 - 3295
  • [6] Acyl Radicals from Aromatic Carboxylic Acids by Means of Visible-Light Photoredox Catalysis
    Bergonzini, Giulia
    Cassani, Carlo
    Wallentin, Carl-Johan
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (47) : 14066 - 14069
  • [7] Estimation of standard reduction potentials of alkyl radicals involved in atom transfer radical polymerization
    Bortolamei, Nicola
    Isse, Abdirisak A.
    Gennaro, Armando
    [J]. ELECTROCHIMICA ACTA, 2010, 55 (27) : 8312 - 8318
  • [8] MECHANISTIC PHOTOCHEMISTRY OF ACYLSILANES .1. REACTION WITH ALCOHOLS
    BOURQUE, RA
    DAVIS, PD
    DALTON, JC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (03) : 697 - 699
  • [9] Vinylpyridines as Building Blocks for the Photocatalyzed Synthesis of Alkylpyridines
    Capaldo, Luca
    Fagnoni, Maurizio
    Ravelli, Davide
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (27) : 6527 - 6530
  • [10] Smooth Photocatalyzed Benzylation of Electrophilic Olefins via Decarboxylation of Arylacetic Acids
    Capaldo, Luca
    Buzzetti, Luca
    Merli, Daniele
    Fagnoni, Maurizio
    Ravelli, Davide
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (16) : 7102 - 7109
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