Difunctionalization of gem-Difluoroalkenes via Photoredox Catalysis: Synthesis of Diverse α,α-Difluoromethyl-β-alkoxysulfones

被引：19
|
作者：
Zhu, Wenjuan [1 ,2 ]
Xi, Hui [3 ]
Jiao, Wenyang [1 ,2 ]
Huang, Lihua [1 ,2 ]
Wang, Lianjie [1 ,2 ]
Wu, Junliang [1 ,2 ]
机构：
[1] Zhengzhou Univ, Coll Chem, Zhengzhou 450001, Peoples R China
[2] Zhengzhou Univ, Inst Green Catalysis, Zhengzhou 450001, Peoples R China
[3] China Natl Tobacco Co, Zhengzhou Tobacco Res Inst, Zhengzhou 450001, Peoples R China
来源：
ORGANIC LETTERS | 2022年 / 24卷 / 02期
关键词：
STEREOSELECTIVE-SYNTHESIS; ALKENES; ACIDS; DIFLUOROMETHYLATION; ALKYLATION; ACTIVATION; SECONDARY; FLUORINE; TERTIARY; ALKYNES;
D O I：
10.1021/acs.orglett.1c04165
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Visible-light-promoted alkoxysulfonylation of gem-difluoroalkenes using sulfonyl chlorides and alcohols has been developed. The reaction exhibits a relatively broad substrate scope with excellent functional group compatibility. This synthesis method includes an atom transfer radical addition-like process. The products can be used as platform molecules for further modification.
引用
收藏
页码：720 / 725
页数：6
相关论文
共 50 条
  • [1] Accessing gem-difluoroalkenes via photoredox catalysis
    Wiles, Rebecca
    Lang, Simon
    Kelly, Christopher
    Molander, Gary
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 254
  • [2] Synthesis of gem-difluoroalkenes via photoredox-catalyzed defluoroaryloxymethylation of α-trifluoromethyl alkenes
    Atriardi, Shafrizal Rasyid
    Kim, Jae-Young
    Anita, Yulia
    Woo, Sang Kook
    [J]. BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2023, 44 (01) : 50 - 54
  • [3] Photoredox-Catalyzed Difunctionalization of Unactivated Olefins for Synthesizing Lactam-Substituted gem-Difluoroalkenes
    Shi, Jie
    Guo, Li-Yun
    Hu, Qu-Ping
    Liu, Yu-Tao
    Li, Qing
    Pan, Fei
    [J]. ORGANIC LETTERS, 2021, 23 (22) : 8822 - 8827
  • [4] Desulfonylative Coupling of Alkylsulfones with gem-Difluoroalkenes by Visible-Light Photoredox Catalysis
    Nambo, Masakazu
    Ghosh, Koushik
    Yim, Jacky C. -H.
    Tahara, Yasuyo
    Inai, Naoto
    Yanai, Takeshi
    Crudden, Cathleen M.
    [J]. ACS CATALYSIS, 2022, 12 (15) : 9526 - 9532
  • [5] Difunctionalization of gem-difluoroalkenes for amination and heteroarylation via metal-free photocatalysis
    Zhong, Yuanchen
    Zhuang, Zhen
    Zhang, Xiaofei
    Xu, Bin
    Yang, Chunhao
    [J]. CHEMICAL COMMUNICATIONS, 2024, 60 (36) : 4830 - 4833
  • [6] Autocatalytic Synthesis of Thioesters via Thiocarbonylation of gem-Difluoroalkenes
    Jiang, Xinpeng
    Wang, Guan
    Zheng, Zicong
    Yu, Xiaohui
    Hong, Ye
    Xia, Haoqi
    Yu, Chuanming
    [J]. ORGANIC LETTERS, 2020, 22 (24) : 9762 - 9766
  • [7] Photoredox Catalyzed Synthesis of gem-Difluoroalkenes and Monofluorinated Cyclooctenes via 1,5-HAT Process
    Li, Yuan-Bo
    Wang, Yu-Lin
    Gao, Qian
    Dai, Jing-Cheng
    Jin, Ruo-Xing
    Wang, Xi-Sheng
    [J]. ORGANIC LETTERS, 2024, 26 (21) : 4548 - 4553
  • [8] Synthesis of gem-Difluoroalkenes via β-Fluoride Elimination of Organorhodium(I)
    Miura, Tomoya
    Ito, Yoshiteru
    Murakami, Masahiro
    [J]. CHEMISTRY LETTERS, 2008, 37 (09) : 1006 - 1007
  • [9] Access to gem-Difluoroalkenes via Organic Photoredox-Catalyzed gem-Difluoroallylation of Alkyl Iodides
    Yan, Songlin
    Yu, Weijie
    Zhang, Jianye
    Fan, Hongmei
    Lu, Zhifeng
    Zhang, Zhenming
    Wang, Tao
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (02): : 1574 - 1584
  • [10] Electrochemical synthesis of functionalized gem-difluoroalkenes with diverse alkyl sources via a defluorinative alkylation process
    Zhang, Haoxiang
    Liang, Mengze
    Zhang, Xiao
    He, Meng-Ke
    Yang, Chao
    Guo, Lin
    Xia, Wujiong
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2021, 9 (01) : 95 - 101
12345