Visible-Light-Induced Synthesis of γ-Amino Sulfones from Vinyl Sulfones and Amino Acids

被引:1
|
作者
Qian, Zhu-Ming [1 ]
Wang, Feng-Yu [1 ]
Guan, Zhi [1 ]
He, Yan-Hong [1 ]
机构
[1] Southwest Univ, Sch Chem & Chem Engn, Key Lab Appl Chem Chongqing Municipal, Chongqing 400715, Peoples R China
基金
中国国家自然科学基金;
关键词
photochemistry; gamma-amino sulfone; vinyl sulfone; amino acid; decarboxylation; FUNCTIONALIZATION; DERIVATIVES; INHIBITORS; RADICALS;
D O I
10.1002/adsc.202400432
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A method for the synthesis of gamma-amino sulfones through visible light-induced oxidative decarboxylation and radical reductive addition is described. Various readily available N-protected natural amino acids react with aromatic/aliphatic vinyl sulfones to directly produce gamma-amino sulfone derivatives. This reaction is also applicable to alpha-N(O)-acids and other aliphatic carboxylic acids, resulting in the corresponding sulfone derivatives. The method operates without the need for sacrificial reducing agents or additional hydrogen atom donors. The sole by-product is CO2 released from decarboxylation, rendering the process both atom- and step-economical. image
引用
收藏
页码:3022 / 3028
页数:7
相关论文
共 50 条
  • [1] Visible-Light-Induced Chemoselective Synthesis of α-Chloro and Vinyl Sulfones by Sulfonylation of Alkenes
    Niu, Teng-fei
    Lin, Dan
    Xue, Lin-shuang
    Jiang, Ding-yun
    Ni, Bang-qing
    SYNLETT, 2018, 29 (03) : 364 - 368
  • [2] Visible-Light-Induced Synthesis of Vinyl Sulfones via Decarboxylative Sulfonylation of Cinnamic Acids Using Sulfonylazides/p-Toluenesulfonylmethyl Isocyanide/β-Keto Sulfones
    Ishu, Km
    Kumar, Mahesh
    Singh, Krishna Nand
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (15): : 10919 - 10928
  • [3] Photocatalyst-free visible light driven synthesis of (E)-vinyl sulfones from cinnamic acids and arylazo sulfones
    Chawla, Ruchi
    Jaiswal, Shefali
    Dutta, P. K.
    Yadav, Lal Dhar S.
    TETRAHEDRON LETTERS, 2020, 61 (22)
  • [4] Synthesis of beta-amino-alpha,alpha-dichloro sulfones from vinyl sulfones
    Jung, JH
    Lee, JW
    Lee, CW
    Oh, DY
    SYNTHETIC COMMUNICATIONS, 1996, 26 (20) : 3715 - 3718
  • [5] Enantiodivergent, catalytic asymmetric synthesis of γ-amino vinyl sulfones
    Picó, A
    Moyano, A
    Pericàas, MA
    JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (13): : 5075 - 5083
  • [6] Visible-Light-Induced Reductive Coupling of Arylacetylenes with Benzothiazole Sulfones
    Sengoku, Tetsuya
    Iwama, Haruka
    Shimotori, Takuma
    Fujimoto, Keisuke
    Inuzuka, Toshiyasu
    Matsune, Koki
    Yoda, Hidemi
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (17): : 12776 - 12782
  • [7] Synthesis of Vinyl Sulfones through Visible Light-Induced Decarboxylative Sulfonylation of Cinnamic Acids with Disulfides
    Li, Xuezhi
    Wang, Min
    Wang, Zhihui
    Wang, Lei
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 8 (08) : 1426 - 1435
  • [8] Photosensitizer-free synthesis of β-keto sulfones via visible-light-induced oxysulfonylation of alkenes with sulfonic acids
    Peng, Zhen
    Hong, Yun-Yun
    Peng, Sha
    Xu, Xiang-Qun
    Tang, Shan-Shan
    Yang, Li-Hua
    Xie, Long-Yong
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (20) : 4537 - 4541
  • [9] Visible-light-induced remote C(sp3)-H sulfonylvinylation: assembly of cyanoalkylated vinyl sulfones
    Bao, Ping
    Yu, Feiyan
    He, Fu-Sheng
    Tang, Zhimei
    Deng, Wei-Ping
    Wu, Jie
    ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (17) : 4820 - 4825
  • [10] AMINO SULFIDES AND AMINO SULFONES .22. REACTION OF SULFONEMETHYLATION OF AMINO ACIDS
    FELDMAN, IK
    JOURNAL OF GENERAL CHEMISTRY USSR, 1962, 32 (04): : 1022 - &