Reductive Desulfonylation of Sulfonamides under Polysulfide Anions Photocatalysis

被引:0
|
作者
Feng, Zixuan [1 ]
Tan, Eugene Yew Kun [1 ]
Chiba, Shunsuke [1 ]
机构
[1] Nanyang Technol Univ, Sch Chem Chem Engn & Biotechnol, Singapore 637371, Singapore
关键词
ELECTRON-TRANSFER; PROTECTING GROUP; DEPROTECTION; CLEAVAGE; AMINES; MILD; ARENESULFONAMIDES; NITROGEN; ESTERS; AMIDES;
D O I
10.1021/acs.orglett.5c01013
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We demonstrate that polysulfide anions are capable of catalyzing desulfonylation of sulfonamides having a series of aryl and alkyl substituents in the presence of potassium formate under irradiation with visible light. The developed protocol is operationally concise and cost-effective, representing a practical and sustainable synthetic tool for desulfonylation and expanding the chemical space in secondary amine synthesis.
引用
收藏
页码:4026 / 4031
页数:6
相关论文
共 50 条
  • [1] Primary and Secondary Amines by Flavin-Photocatalyzed Consecutive Desulfonylation and Dealkylation of Sulfonamides
    Pavlovska, Tetiana
    Weisheitelova, Ivana
    Pramthaisong, Chiranan
    Sikorski, Marek
    Jahn, Ullrich
    Cibulka, Radek
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (24) : 4662 - 4671
  • [2] Electron Transfer Photoredox Catalysis: Development of a Photoactivated Reductive Desulfonylation of an Aza-Heteroaromatic Ring
    Qiang-Liu
    Liu, Yu-Xiu
    Song, Hong-Jian
    Wang, Qing-Min
    ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (15) : 3110 - 3115
  • [3] Ti(O-i-Pr)4/Me3SiCl/Mg-Mediated Reductive Cleavage of Sulfonamides and Sulfonates to Amines and Alcohols
    Shohji, Noriaki
    Kawaji, Tsuyoshi
    Okamoto, Sentaro
    ORGANIC LETTERS, 2011, 13 (10) : 2626 - 2629
  • [4] Asymmetric Stepwise Reductive Amination of Sulfonamides, Sulfamates, and a Phosphinamide by Nickel Catalysis
    Zhao, Xiaohu
    Xu, Haiyan
    Huang, Xiaolei
    Zhou, Jianrong Steve
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (01) : 292 - 296
  • [5] Light-Driven Reductive Cleavage of Sulfonamides Promoted by Thiourea Organophotosensitizers
    Brom, Jules
    Maruani, Antoine
    Micouin, Laurent
    Benedetti, Erica
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (09) : 5923 - 5935
  • [6] Nitro-sulfinate Reductive Coupling to Access (Hetero)aryl Sulfonamides
    Gatarz, Sandra E.
    Griffiths, Oliver M.
    Esteves, Henrique A.
    Jiao, Wenhua
    Morse, Peter
    Fisher, Ethan L.
    Blakemore, David C.
    Ley, Steven V.
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (03) : 1898 - 1909
  • [7] Desulfonylation of Tosyl Amides through Catalytic Photoredox Cleavage of NS Bond Under Visible-Light Irradiation
    Xuan, Jun
    Li, Bin-Jie
    Feng, Zhu-Jia
    Sun, Guo-Dong
    Ma, Huan-Huan
    Yuan, Zhi-Wei
    Chen, Jia-Rong
    Lu, Liang-Qiu
    Xiao, Wen-Jing
    CHEMISTRY-AN ASIAN JOURNAL, 2013, 8 (06) : 1090 - 1094
  • [8] Reductive Cleavage of Secondary Sulfonamides: Converting Terminal Functional Groups into Versatile Synthetic Handles
    Fier, Patrick S.
    Kim, Suhong
    Maloney, Kevin M.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (46) : 18416 - 18420
  • [9] Selective cleavage of the N-propargyl group from sulfonamides and amides under ruthenium catalysis
    Wang, Jingjing
    Li, Feng
    Pei, Wenlong
    Yang, Mixue
    Wu, Yidan
    Ma, Danyang
    Zhang, Furong
    Wang, Jianhui
    TETRAHEDRON LETTERS, 2018, 59 (20) : 1902 - 1905
  • [10] Nitric oxide emission during the reductive heterogeneous photocatalysis of aqueous nitrate with TiO2
    Nahuel Montesinos, V.
    Quici, Natalia
    Destaillats, Hugo
    Litter, Marta I.
    RSC ADVANCES, 2015, 5 (104): : 85319 - 85322