Metal-free photosensitized aminosulfonylation of alkenes: a practical approach to β-amido sulfones

被引:20
|
作者
Chen, Meiling [1 ]
Sun, Wenyan [1 ]
Yang, Jingjing [1 ]
Yuan, LuLu [1 ]
Chen, Jian-Qiang [1 ]
Wu, Jie [1 ,2 ,3 ]
机构
[1] Taizhou Univ, Inst Adv Studies, Sch Pharmaceut & Chem Engn, 1139 Shifu Ave, Taizhou 318000, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
[3] Henan Normal Univ, Sch Chem & Chem Engn, Xinxiang 453007, Peoples R China
基金
中国国家自然科学基金;
关键词
AZA-MICHAEL ADDITION; AMINO SULFONES; STEREOSELECTIVE-SYNTHESIS; SULFUR-DIOXIDE; ENANTIOSELECTIVE SYNTHESIS; INHIBITOR; POTENT; APREMILAST; DISCOVERY; PHOSPHODIESTERASE-4;
D O I
10.1039/d3gc01059g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A general and environmentally friendly organic photo-induced strategy was developed for the synthesis of diverse alkyl-substituted beta-amino sulfone derivatives, including primary, secondary, and tertiary alkyl-substituted products. Various carboxylic acid derivatives from the simplest acetic acid to sterically bulky tertiary acids can participate in this transformation.
引用
收藏
页码:3857 / 3863
页数:7
相关论文
共 50 条
  • [1] Metal-Free Synthesis of Imido Derivatives by Direct Oxidation of α-Amido Sulfones
    Martinelli, Fabio
    Palmieri, Alessandro
    Petrini, Marino
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (26) : 5085 - 5089
  • [2] Metal-Free Amino(hetero)arylation and Aminosulfonylation of Alkenes Enabled by Photoinduced Energy Transfer
    Qi, Xu-Kuan
    Zheng, Meng-Jie
    Yang, Chao
    Zhao, Yating
    Guo, Lin
    Xia, Wujiong
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023, 145 (30) : 16630 - 16641
  • [3] Metal-free photosensitized oxyimination of unactivated alkenes with bifunctional oxime carbonates
    Patra, Tuhin
    Das, Mowpriya
    Daniliuc, Constantin G.
    Glorius, Frank
    NATURE CATALYSIS, 2021, 4 (01) : 54 - 61
  • [4] Metal-free photosensitized oxyimination of unactivated alkenes with bifunctional oxime carbonates
    Tuhin Patra
    Mowpriya Das
    Constantin G. Daniliuc
    Frank Glorius
    Nature Catalysis, 2021, 4 : 54 - 61
  • [5] Correction to "Metal-Free Amino(hetero)arylation and Aminosulfonylation of Alkenes Enabled by Photoinduced Energy Transfer"
    Qi, Xu-Kuan
    Zheng, Meng-Jie
    Yang, Chao
    Zhao, Yating
    Guo, Lin
    Xia, Wujiong
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023, 145 (40) : 22285 - 22286
  • [6] Functionalization of Alkynes and Alkenes Using a Cascade Reaction Approach: Synthesis of β-Keto Sulfones under Metal-free Conditions
    Kumar, Mukesh
    Ahmed, Riyaz
    Singh, Maninder
    Sharma, Shweta
    Thatikonda, Thanusha
    Singh, Parvinder Pal
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (02): : 716 - 725
  • [7] Regioselective Access to Vicinal Diamines by Metal-Free Photosensitized Amidylimination of Alkenes with Oxime Esters
    Zheng, Yu
    Wang, Zhu-Jun
    Ye, Zhi-Peng
    Tang, Kai
    Xie, Zhen-Zhen
    Xiao, Jun-An
    Xiang, Hao-Yue
    Chen, Kai
    Chen, Xiao-Qing
    Yang, Hua
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (44)
  • [8] Metal-free Oxidative Coupling of Aromatic Alkenes with Thiols Leading to (E)-Vinyl Sulfones
    Wang, Leilei
    Yue, Huilan
    Yang, Daoshan
    Cui, Huanhuan
    Zhu, Minghui
    Wang, Jinming
    Wei, Wei
    Wang, Hua
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (13): : 6857 - 6864
  • [9] A metal-free and regioselective approach to (Z)-β-fluorovinyl sulfones and their chemoselective hydrogenation to β-fluoroalkyl sulfones
    Sedgwick, Daniel M.
    Roman, Raquel
    Barrio, Pablo
    Morales, Cristina
    Fustero, Santos
    JOURNAL OF FLUORINE CHEMISTRY, 2018, 206 : 108 - 116
  • [10] Metal-Free Trifluoromethylthiolation of Arylazo Sulfones
    Li, Ankun
    Li, Yuxuan
    Liu, Junjie
    Chen, Jingqi
    Lu, Kui
    Qiu, Di
    Fagnoni, Maurizio
    Protti, Stefano
    Zhao, Xia
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (01): : 1292 - 1299