Transition-metal-free NaI-mediated reaction of aryl sulfonyl chloride with alkynes: Synthesis of (E)-β-iodovinyl sulfones

被引:6
|
作者
Chen, Dan [1 ]
Lin, Li [1 ]
Peng, Xiaoyan [1 ]
Yu, Xinyi [1 ]
Yang, Zhonglie [1 ]
Liu, Yutong [1 ]
Zhang, Xiaobin [2 ]
Li, Jiahong [1 ]
Jiang, Hezhong [1 ]
机构
[1] Southwest Jiaotong Univ, Sch Life Sci & Engn, Chengdu 610031, Peoples R China
[2] Sichuan Inst Atom Energy, Radiat Chem Dept, Irradiat Preservat Key Lab Sichuan Prov, Chengdu 610100, Peoples R China
基金
中国国家自然科学基金;
关键词
Alkynes; Arylsulfuryl chlorides; (E)-beta-iodovinyl sulfones; NaI-mediated; Transition-metal-free; BETA-KETO SULFONES; ONE-POT SYNTHESIS; VINYL SULFONES; EFFICIENT SYNTHESIS; CONJUGATE ADDITION; MICHAEL REACTIONS; ALKENES; ACCESS; IODOSULFONYLATION; CYCLOADDITION;
D O I
10.1016/j.tetlet.2021.153203
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel protocol for synthesis of (E)-beta-Iodovinyl sulfones via NaI-mediated of aryl sulfonyl chloride with alkynes is described, featuring transition-metal-free condition, commercial available substrates, convenient operation, as well as good functional group compatibility. A wide variety of substrate application and good functional group tolerance is provided by this approach, giving multiple (E)-beta-Iodovinyl sulfones analogues with excellent yields (up to 98%, >4 g scale). (C) 2021 Elsevier Ltd. All rights reserved.
引用
收藏
页数:5
相关论文
共 50 条
  • [1] CAN mediated reaction of aryl sulfinates with alkenes and alkynes:: Synthesis of vinyl sulfones, β-iodovinyl sulfones and acetylenic sulfones
    Nair, V
    Augustine, A
    Suja, TD
    [J]. SYNTHESIS-STUTTGART, 2002, (15): : 2259 - 2265
  • [2] I2/TBHP-mediated reaction of sulfonylhydrazides with alkynes: synthesis of (E)-β-iodovinyl sulfones
    Li, Xiaoqing
    Xu, Xiangsheng
    Shi, Xinhua
    [J]. TETRAHEDRON LETTERS, 2013, 54 (24) : 3071 - 3074
  • [3] PhI(OAc)2/KI-Mediated Reaction of Aryl Sulfinates with Alkenes, Alkynes, and α,β-Unsaturated Carbonyl Compounds: Synthesis of Vinyl Sulfones and β-Iodovinyl Sulfones
    Katrun, Praewpan
    Chiampanichayakul, Supanimit
    Korworapan, Kanokwan
    Pohmakotr, Manat
    Reutrakul, Vichai
    Jaipetch, Thaworn
    Kuhakarn, Chutima
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (29) : 5633 - 5641
  • [4] KI as iodine source for the synthesis of E-iodovinyl sulfones via metal-free iodosulfonylation of terminal alkynes
    Yang, Lu
    Hu, Deqing
    Wei, Li
    Liu, Yunyun
    [J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2017, 192 (12) : 1301 - 1304
  • [5] Transition-Metal-Free Synthesis of (E)-Vinyl Sulfones from Vinyl Halides in Water
    Liang, Shuai
    Zhang, Ruo-Yi
    Wang, Gao
    Chen, Shan-Yong
    Yu, Xiao-Qi
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (31) : 7050 - 7053
  • [6] Transition-Metal-Free Approach for the Synthesis of 4-Aryl-quinolines from Alkynes and Anilines
    Phanindrudu, Mandalaparthi
    Wakade, Sandip Balasaheb
    Tiwari, Dipak Kumar
    Likhar, Pravin R.
    Tiwari, Dharmendra Kumar
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (16): : 9137 - 9143
  • [7] Synthesis of (E)-β-Iodovinyl Sulfones via HI-mediated Vicinal Iodosulfonylation of Alkynes with Sodium Sulfinates
    Chen, Zu-Jia
    Zeng, Yu
    Li, Zhong-Hao
    Li, Huan-Qing
    Yu, Shi-Wei
    Shen, Qing
    Wang, Zhao-Yang
    [J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 13 (06)
  • [8] One-pot transition-metal-free synthesis of alkynes and enynes
    Gu, Yuanyun
    Wu, Yu
    Wang, Yan-En
    Phadnis, Nidheesh
    Xiong, Dan
    Mao, Jianyou
    Walsh, Patrick J.
    [J]. CELL REPORTS PHYSICAL SCIENCE, 2024, 5 (08):
  • [9] Facile Synthesis of Sulfonyl Amidines and β-Amino Sulfonyl Enamines under Transition-Metal-Free Conditions
    Gao, Tingting
    Zhao, Mingming
    Meng, Xu
    Li, Chuanbin
    Chen, Baohua
    [J]. SYNLETT, 2011, (09) : 1281 - 1284
  • [10] Transition-Metal-Free Acid-Mediated Synthesis of Aryl Sulfides from Thiols and Thioethers
    Wagner, Anna M.
    Sanford, Melanie S.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (05): : 2263 - 2267