Visible Light-Promoted Friedel-Crafts-Type Chloroacylation of Alkenes to β-Chloroketones

被引：26
|
作者：
Patil, Dilip V. [1 ]
Kim, Hun Young [1 ]
Oh, Kyungsoo [1 ]
机构：
[1] Chung Ang Univ, Ctr Metareceptome Res, Grad Sch Pharmaceut Sci, Seoul 06974, South Korea
来源：
ORGANIC LETTERS | 2020年 / 22卷 / 08期
基金：
新加坡国家研究基金会;
关键词：
CHLOROVINYL KETONES; ACYLATION; CHLORIDES; CHEMISTRY;
D O I：
10.1021/acs.orglett.0c00788
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The photoredox chloroacylation of alkenes has been developed as a substitute for the Friedel-Crafts acylation of alkenes to beta-chloroketones. The direct generation of acyl radical species from acid chlorides under the photoredox conditions allows the formation of beta-chloroketones without dehydrochlorination with the help of KHCO3. The synthetic utility of the current method is demonstrated in the one-pot synthesis of dihydroisoxazole, dihydropyrazole, and dihydropyrimidine-2-thione in 1 mmol scale.
引用
收藏
页码：3018 / 3022
页数：5
相关论文
共 50 条
  • [21] Visible Light-Promoted Three-Component Carboazidation of Unactivated Alkenes with TMSN3 and Acrylonitrile
    Yang, Bo
    Ren, Xiang
    Shen, Xuzhong
    Li, Tongtong
    Lu, Zhan
    CHINESE JOURNAL OF CHEMISTRY, 2018, 36 (11) : 1017 - 1023
  • [22] Designing radical chemistry by visible light-promoted homolysis
    Protti, Stefano
    Ravelli, Davide
    Fagnoni, Maurizio
    TRENDS IN CHEMISTRY, 2022, 4 (04): : 305 - 317
  • [23] Bronsted Acid Catalyzed Oxygenative Bimolecular Friedel-Crafts-type Coupling of Ynamides
    Patil, Dilip V.
    Kim, Seung Woo
    Nguyen, Quynh H.
    Kim, Hanbyul
    Wang, Shan
    Hoang, Tuan
    Shin, Seunghoon
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (13) : 3670 - 3674
  • [24] Friedel-Crafts-type mechanism for the enzymatic elimination of ammonia from histicline and phenylalanine
    Poppe, L
    Rétey, J
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (24) : 3668 - 3688
  • [25] FRIEDEL-CRAFTS-TYPE REACTION OF BENZALDEHYDE WITH BENZENE - DIPROTONATED BENZALDEHYDE AS THE REACTIVE INTERMEDIATE
    SAITO, S
    OHWADA, T
    SHUDO, K
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (45) : 11081 - 11084
  • [26] First asymmetric synthesis of (-)-lintetralin via intramolecular Friedel-Crafts-type cyclization
    Enders, D
    del Signore, G
    Berner, OM
    CHIRALITY, 2003, 15 (06) : 510 - 513
  • [27] Comparison of the Catalytic Activity of Copper Nanostructures in Friedel-Crafts-Type Condensation Reactions
    Saiadian, Shohreh
    Khorshidi, Alireza
    CHEMISTRYSELECT, 2018, 3 (01): : 142 - 146
  • [28] Visible light-promoted dihydroxylation of styrenes with water and dioxygen
    Yang, Bo
    Lu, Zhan
    CHEMICAL COMMUNICATIONS, 2017, 53 (94) : 12634 - 12637
  • [29] Visible Light-Promoted Radical Reactions of Diazo Compounds
    Li Sen
    Zhou Lei
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2022, 42 (12) : 3944 - 3958
  • [30] Bronsted Acid Catalyzed Friedel-Crafts-Type Coupling and Dedinitrogenation Reactions of Vinyldiazo Compounds
    Zheng, Haifeng
    Dong, Kuiyong
    Wherritt, Daniel
    Arman, Hadi
    Doyle, Michael P.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (32) : 13613 - 13617
12345