Nickel-catalyzed tandem coupling of allyl electrophiles, alkynes, and alkynyltins

被引:31
|
作者
Cui, DM [1 ]
Tsuzuki, T [1 ]
Miyake, K [1 ]
Ikeda, S [1 ]
Sato, Y [1 ]
机构
[1] Nagoya City Univ, Dept Pharmaceut Sci, Mizuho Ku, Nagoya, Aichi 467, Japan
关键词
D O I
10.1016/S0040-4020(97)10207-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The nickel-catalyzed intermolecular coupling of allyl acetate or allyl carbonate with alkynes and alkynyltins was carried out in the presence of LiCl to give 3,6-dien-1-yne regio-and stereoselectively. On the other hand, the intramolecular cyclization and coupling of omega-alkynyl electrophiles with alkynyltins gave five-membered cyclic products. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1063 / 1072
页数:10
相关论文
共 50 条
  • [21] Coupling of alkynes and aryl halides with nickel-catalyzed Sonogashira reactions
    Chen, Hui
    Yao, Licheng
    Guo, Lin
    Liu, Yahu A.
    Tian, Boxue
    Liao, Xuebin
    CELL REPORTS PHYSICAL SCIENCE, 2023, 4 (09):
  • [22] Nickel-Catalyzed Reductive Coupling of Aldehydes with Alkynes Mediated by Alcohol
    Zheng, Yan-Long
    Ye, Mengchun
    CHINESE JOURNAL OF CHEMISTRY, 2020, 38 (05) : 489 - 493
  • [23] Nickel-Catalyzed Amination of Alkyl Electrophiles
    Wang, Qing
    Tao, Xiangzhang
    Ni, Shengyang
    Pan, Yi
    Wang, Yi
    ORGANIC LETTERS, 2023, 25 (31) : 5822 - 5826
  • [24] Nickel-Catalyzed Hydroimination of Alkynes
    Manan, Rajith S.
    Kilaru, Praveen
    Zhao, Pinjing
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (19) : 6136 - 6139
  • [25] Nickel-catalyzed carbocyanation of alkynes
    Nakao, Yoshiaki
    Hiyama, Tamejiro
    PURE AND APPLIED CHEMISTRY, 2008, 80 (05) : 1097 - 1107
  • [26] ENANTIOSELECTIVE NICKEL-CATALYZED GRIGNARD CROSS-COUPLING OF ALLYL ELECTROPHILES - THE INFLUENCE OF THE ALKYL GROUP OF THE GRIGNARD-REAGENT
    INDOLESE, AF
    CONSIGLIO, G
    ORGANOMETALLICS, 1994, 13 (06) : 2230 - 2234
  • [27] Tandem coupling of allyl electrophiles, alkynes, and Me3Al or Me2Zn in the presence of a nickel catalyst
    Ikeda, S
    Miyashita, H
    Sato, Y
    ORGANOMETALLICS, 1998, 17 (19) : 4316 - 4318
  • [28] Nickel-Catalyzed Reductive C-Ge Coupling of Carbon Electrophiles with Chlorogermanes
    He, Fusheng
    Wu, Jie
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2022, 42 (01) : 312 - 313
  • [29] Nickel-catalyzed reductive coupling of alkynes and sterically encumbered terminal epoxides
    Byers, Jeffery Allen
    Jamison, Timothy F.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 241
  • [30] Nickel-Catalyzed Cross-Coupling of Organolithium Reagents with (Hetero)Aryl Electrophiles
    Heijnen, Dorus
    Gualtierotti, Jean-Baptiste
    Hornillos, Valentin
    Feringa, Ben L.
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (12) : 3991 - 3995