Copper-catalyzed regioselective 1,4-sulfonylcyanation of 1,3-enynes with sulfonyl chlorides and TMSCN

被引:18
|
作者
Lv, Yunhe [1 ]
Han, Wanru [1 ]
Pu, Weiya [1 ]
Xie, Jinhui [1 ]
Wang, Axue [1 ]
Zhang, Mengyue [1 ]
Wang, Jin [1 ]
Lai, Junrong [1 ]
机构
[1] Anyang Normal Univ, Coll Chem & Chem Engn, Anyang 455000, Peoples R China
来源
ORGANIC CHEMISTRY FRONTIERS | 2022年 / 9卷 / 14期
基金
中国国家自然科学基金;
关键词
ALKYNES; AMINODIFLUOROALKYLATION; FUNCTIONALIZATION; ALKENES;
D O I
10.1039/d2qo00486k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel and practical copper-catalyzed reaction for the 1,4-sulfonylcyanation of 1,3-enynes under mild conditions is described. This protocol provides efficient and straightforward access to a variety of 5-sulfonylpenta-2,3-dienenitrile derivatives with excellent functional group tolerance and good regioselectivity from readily available 1,3-enynes and commercially available sulfonyl chlorides and TMSCN. A mechanism involving sulfonyl and allenyl radical species is proposed.
引用
收藏
页码:3775 / 3780
页数:6
相关论文
共 50 条
  • [21] Copper-catalyzed 1,4-silylcyanation of 1,3-enynes: A silyl radical-initiated approach for synthesis of difunctionalized allenes
    Li, Qi
    Wang, Zi-Lu
    Xu, Yun-He
    CHINESE CHEMICAL LETTERS, 2025, 36 (03)
  • [22] Copper-Catalyzed Sulfonyl Radical-Enabled Regioselective Cyclization of 1,6-Enynes
    Zhang, Jun-Yao
    Bao, Wen-Hui
    Qin, Fu-Hua
    Lei, Ke-Wei
    Li, Qiang
    Wei, Wen-Ting
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 8 (11) : 2050 - 2053
  • [23] Copper-catalyzed 1,4-silylcyanation of 1,3-enynes: A silyl radical-initiated approach for synthesis of difunctionalized allenes
    Qi Li
    Zi-Lu Wang
    Yun-He Xu
    Chinese Chemical Letters, 2025, 36 (03) : 305 - 309
  • [24] Cu-catalyzed regioselective diborylation of 1,3-enynes for the efficient synthesis of 1,4-diborylated allenes
    Wujun Jian
    Mong-Feng Chiou
    Yajun Li
    Hongli Bao
    Song Yang
    Chinese Chemical Letters, 2024, 35 (05) : 167 - 170
  • [25] Cu-catalyzed regioselective diborylation of 1,3-enynes for the efficient synthesis of 1,4-diborylated allenes
    Jian, Wujun
    Chiou, Mong-Feng
    Li, Yajun
    Bao, Hongli
    Yang, Song
    CHINESE CHEMICAL LETTERS, 2024, 35 (05)
  • [26] Copper/Di-tert-butyl Peroxide-Catalyzed Regioselective Hydroxyphosphorylation of 1,3-Enynes
    Zhu, Shaoqun
    Wang, Jiawei
    Zhou, Bing
    Hou, Hong
    SYNTHESIS-STUTTGART, 2021, 53 (20): : 3751 - 3759
  • [27] Metal-Free Highly Regioselective 1,4-Sulfonyliodination of 1,3-Enynes
    Lv, Yunhe
    Lai, Junrong
    Pu, Weiya
    Wang, Jin
    Han, Wanru
    Wang, Axue
    Zhang, Mengyue
    Wang, Xue
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (04): : 2034 - 2045
  • [28] Regio- and Stereoselective Copper-Catalyzed Borylation-Protodeboronation of 1,3-Diynes: Access to (Z)-1,3-Enynes
    Burgio, Ariel L.
    Buchbinder, Nicklas W.
    Santos, Webster L.
    ORGANIC LETTERS, 2023, 25 (15) : 2652 - 2656
  • [29] NHC and photoredox co-catalyzed 1,4-alkylcarbonylation of 1,3-enynes
    Zhang, Zhaoyang
    Yang, Jia-Yi
    Li, Shihao
    Li, Xiao-Xuan
    Feng, Yi-Si
    ORGANIC CHEMISTRY FRONTIERS, 2025,
  • [30] Enantio- and Diastereoselective Synthesis of Homopropargyl Amines by Copper-Catalyzed Coupling of Imines, 1,3-Enynes, and Diborons
    Manna, Srimanta
    Dherbassy, Quentin
    Perry, Gregory J. P.
    Procter, David J.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (12) : 4879 - 4882