Radical Hydro-Fluorosulfonylation of Propargylic Alcohols via Electron Donor-Acceptor Photoactivation

被引:9
|
作者
Zhang, Yingyin [1 ]
Feng, Qingyuan [1 ]
Zheng, Yu [1 ]
Lu, Yanju [1 ]
Liao, Saihu [2 ]
Huang, Shenlin [1 ,3 ]
机构
[1] Nanjing Forestry Univ, Jiangsu Coinnovat Ctr Efficient Proc & Utilizat F, Int Innovat Ctr Forest Chem & Mat, Nanjing 210037, Jiangsu, Peoples R China
[2] Xiamen Univ, State Key Lab Phys Chem Solid Surfaces, Xiamen 361005, Fujian, Peoples R China
[3] Hunan Normal Univ, Coll Chem & Chem Engn, Key Lab Chem Biol & Tradit Chinese Med Res, Minist Educ China, Changsha 410081, Hunan, Peoples R China
基金
中国国家自然科学基金;
关键词
D O I
10.1021/acs.orglett.4c00010
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A radical hydro-fluorosulfonylation of propargyl alcohols with FSO2Cl is presented based on the photoactivation of the electron donor-acceptor (EDA) complex. The reaction avoids the requirement for photocatalysts, bases, hydrogen donor reagents, any other additives, and harsh conditions, enabling the facile synthesis of various functionalized gamma-hydroxy (E)-alkenylsulfonyl fluorides. These multifunctional sulfonyl fluorides can be further diversified, providing access to various privileged molecules of biological relevance.
引用
收藏
页码:1410 / 1415
页数:6
相关论文
共 50 条
  • [41] Synthesis of Sulfur-Containing Trisubstituted Imidazoles by One-Pot, Multicomponent Reaction via Electron Donor-Acceptor Complex Photoactivation
    Zuo, Junze
    Li, Xufeng
    Shi, Yongjia
    Lv, Jian
    Yang, Daoshan
    ORGANIC LETTERS, 2024, 26 (17) : 3541 - 3546
  • [42] ELECTRON DONOR-ACCEPTOR COMPOUNDS .37. COMPLEXATION OF ELECTRON DONOR-ACCEPTOR [2.2]PARACYCLOPHANES WITH TETRACYANOETHYLENE (TCNE)
    SCHANNE, L
    STAAB, HA
    TETRAHEDRON LETTERS, 1984, 25 (16) : 1721 - 1724
  • [43] Radical electrophilic aromatic substitution of electron-deficient aryl halides via aerobic ternary electron donor-acceptor photocatalysis
    Gu, Jiayi
    Meng, Yingfen
    Cheng, Zhuo
    Lu, Guoqing
    Xin, Meixiu
    Tang, Jie
    Du, Zhibo
    Zhang, Xuejing
    Deng, Mingcai
    Zou, Yong
    CELL REPORTS PHYSICAL SCIENCE, 2024, 5 (10):
  • [44] Nickel-Mediated Synthesis of Non-AnomericC-Acyl Glycosidesthrough Electron Donor-Acceptor Complex Photoactivation
    Escolano, Marcos
    Cabrera-Afonso, Maria Jesus
    Ribagorda, Maria
    Badir, Shorouk O.
    Molander, Gary A.
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (07): : 4981 - 4990
  • [45] Effective Formation of New C(sp2)-S Bonds via Photoactivation of Alkylamine-based Electron Donor-Acceptor Complexes
    Herrera-Luna, Jorge C.
    Perez-Aguilar, Maria Carmen
    Gerken, Leon
    Mancheno, Olga Garcia
    Consuelo Jimenez, M.
    Perez-Ruiz, Raul
    CHEMISTRY-A EUROPEAN JOURNAL, 2023, 29 (06)
  • [46] Electron-transfer absorption of sterically bulky donor-acceptor pairs: electron donor-acceptor complexes or random pairs?
    Zhong, C
    Zhou, JW
    Braun, CL
    JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2003, 161 (01) : 1 - 9
  • [47] Catalyst-free C-H methylation of heteroarenes enabled by electron donor-acceptor complex photoactivation
    Wang, Jiayang
    Shao, Baoer
    Ge, Haixia
    Xue, Huiyu
    Ding, Xiangyuan
    Li, Yuqi
    Sheng, Peiyao
    ORGANIC CHEMISTRY FRONTIERS, 2024, 12 (01): : 192 - 199
  • [48] A general arene C–H functionalization strategy via electron donor–acceptor complex photoactivation
    Abhishek Dewanji
    Leendert van Dalsen
    James A. Rossi-Ashton
    Eloise Gasson
    Giacomo E. M. Crisenza
    David J. Procter
    Nature Chemistry, 2023, 15 : 43 - 52
  • [49] Electron Donor-Acceptor Complexes in Perfluoroalkylation Reactions
    Postigo, Al
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (46) : 6391 - 6404
  • [50] RAMAN RESONANCE OF ELECTRON DONOR-ACCEPTOR COMPLEXES
    MICHAELIAN, KH
    RIECKHOFF, KE
    VOIGT, EM
    PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1975, 72 (11) : 4196 - 4199