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

被引:107
|
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%.
引用
收藏
页码:304 / 309
页数:6
相关论文
共 50 条
  • [41] Photoredox-Catalyzed Selective α-Scission of PR3-OH Radicals to Access Hydroalkylation of Alkenes
    Xie, Zhen-Zhen
    Liao, Zi-Hao
    Zheng, Yu
    Yuan, Chu-Ping
    Guan, Jian-Ping
    Li, Ming-Zhi
    Deng, Ke-Yi
    Xiang, Hao-Yue
    Chen, Kai
    Yang, Hua
    ORGANIC LETTERS, 2023, 25 (50) : 9014 - 9019
  • [42] Photoredox-Catalyzed Stereoselective Synthesis of C-Nucleoside Analogues from Glycosyl Bromides and Heteroarenes
    Xia, Liwen
    Fan, Wenjing
    Yuan, Xiang-Ai
    Yu, Shouyun
    ACS CATALYSIS, 2021, 11 (15) : 9397 - 9406
  • [43] Photoredox-Catalyzed Diamidation and Oxidative Amidation of Alkenes: Solvent-Enabled Synthesis of 1,2-Diamides and α-Amino Ketones
    Qin, Qixue
    Han, Yue-Yue
    Jiao, Yan-Yan
    He, Yanyan
    Yu, Shouyan
    ORGANIC LETTERS, 2017, 19 (11) : 2909 - 2912
  • [44] Photoredox-Catalyzed Nucleophilic Aromatic Substitution of Halophenols with Azoles via Oligomeric Phenylene Oxide Radicals
    Seliger, Jan
    Fries, Lydia R.
    Meinhardt, Jonathan M.
    Knowles, Robert R.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2025, 147 (11) : 9931 - 9938
  • [45] Catalytic additions of acylsilanes to imines:: An acyl anion strategy for the direct synthesis of α-amino ketones
    Mattson, AE
    Scheidt, KA
    ORGANIC LETTERS, 2004, 6 (23) : 4363 - 4366
  • [46] Photoredox-catalyzed branch-selective pyridylation of alkenes for the expedient synthesis of Triprolidine
    Shengqing Zhu
    Jian Qin
    Fang Wang
    Huan Li
    Lingling Chu
    Nature Communications, 10
  • [47] Amide Synthesis by Nickel/Photoredox-Catalyzed Direct Carbamoylation of (Hetero)Aryl Bromides
    Alandini, Nurtalya
    Buzzetti, Luca
    Favi, Gianfranco
    Schulte, Tim
    Candish, Lisa
    Collins, Karl D.
    Melchiorre, Paolo
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (13) : 5248 - 5253
  • [48] Photoredox-Catalyzed Strain-Release-Driven Synthesis of Functionalized Spirocyclobutyl Oxindoles
    Singha, Tushar
    Bapat, Nakul Abhay
    Mishra, Subrat Kumar
    Hari, Durga Prasad
    ORGANIC LETTERS, 2024, 26 (30) : 6396 - 6401
  • [49] Organic Photoredox-Catalyzed Hydrosilylation of Vinylboronic Esters for the Synthesis of Geminal and Vicinal Borosilanes
    Zhang, Yue
    Wang, Ting
    Liu, Yuan-Yuan
    Zhang, Zheng-Bing
    Han, Pan
    Jing, Linhai
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (22): : 16463 - 16472
  • [50] Photoredox-Catalyzed Plastic Waste Conversion: Nonselective Degradation versus Selective Synthesis
    Zhang, Yi
    Qi, Ming-Yu
    Tang, Zi-Rong
    Xu, Yi-Jun
    ACS CATALYSIS, 2023, 13 (06) : 3575 - 3590