Nickel-Catalyzed Regio- and Stereoselective Reductive Alkylative Cyclization of 1,6-Enynes with Alkyl Bromides

被引:0
|
作者
Xing, Yunxin [1 ]
Tian, Zhu [1 ]
Shen, Kun [1 ]
机构
[1] Wuhan Univ, Zhongnan Hosp, Sch Pharmaceut Sci, Dept Radiol, Wuhan 430071, Peoples R China
基金
中国国家自然科学基金;
关键词
Reductive cross-coupling; Nickel; Cyclization; 1,6-enyne; ARYLATIVE CYCLIZATION; ALLYL ELECTROPHILES; COUPLING REACTIONS; CASCADE REACTIONS; HALIDES; VINYL;
D O I
10.1002/adsc.202400575
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A nickel-catalyzed reductive alkylative cyclization of 1,6-enynes with alkyl bromides has been developed. This transformation avoids the use of stoichiometric organometallic reagents and introduces alkyl groups regio- and stereoselectively into the products. This method provides a platform for the synthesis of carbo- and heterocycles that are widely found in many natural products and biologically active molecules. image
引用
收藏
页码:3802 / 3807
页数:6
相关论文
共 50 条
  • [1] Nickel-catalyzed electrophiles-controlled enantioselective reductive arylative cyclization and enantiospecific reductive alkylative cyclization of 1,6-enynes
    Liu, Wenfeng
    Xing, Yunxin
    Yan, Denghong
    Kong, Wangqing
    Shen, Kun
    NATURE COMMUNICATIONS, 2024, 15 (01)
  • [2] Nickel-catalyzed reductive cyclization of unactivated 1,6-enynes in the presence of organozinc reagents
    Chen, Mao
    Weng, Yue
    Guo, Mian
    Zhang, Hua
    Lei, Aiwen
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (12) : 2279 - 2282
  • [3] Nickel-Catalyzed Reductive anti-Arylative Cyclization of 1,6-Enynes with Aryl Halides
    Xing Yunxin
    Yan Denghong
    Wen Shun
    Bu Jie
    Shen Kun
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2024, 44 (06) : 1938 - 1948
  • [4] Nickel-Catalyzed Chemo- and Stereoselective Alkenylative Cyclization of 1,6-Enynes with Alkenyl Boronic Acids
    Yang, Chun-Ming
    Mannathan, Subramaniyan
    Cheng, Chien-Hong
    CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (37) : 12212 - 12216
  • [5] Nickel-Catalyzed Enantioselective Reductive Spirocyclization of 1,6-Enynes with o -Bromobenzaldehydes
    Guo, Haoyun
    Chen, Yate
    Kong, Wangqing
    SYNTHESIS-STUTTGART, 2025, 57 (08): : 1448 - 1456
  • [6] Nickel-Catalyzed Hydrosilylation/Cyclization of Difluoro-Substituted 1,6-Enynes
    Takachi, Manabu
    Chatani, Naoto
    ORGANIC LETTERS, 2010, 12 (22) : 5132 - 5134
  • [7] Nickel-catalyzed switchable arylative/endo-cyclization of 1,6-enynes
    Liu, Wenfeng
    Li, Wei
    Xu, Weipeng
    Wang, Minyan
    Kong, Wangqing
    NATURE COMMUNICATIONS, 2024, 15 (01)
  • [8] PALLADIUM-CATALYZED ALKYLATIVE CYCLIZATION OF 1,6-ENYNES AND 1,7-ENYNES
    TROST, BM
    PFRENGLE, W
    URABE, H
    DUMAS, J
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (05) : 1923 - 1924
  • [9] Iron-Catalyzed Reductive Cyclization of 1,6-Enynes
    Lin, Aijun
    Zhang, Zhi-Wei
    Yang, Jiong
    ORGANIC LETTERS, 2014, 16 (02) : 386 - 389
  • [10] Nickel-catalyzed highly chemo- and stereoselective borylative cyclization of 1,6-enynes with bis(pinacolato)diboron
    Hsieh, Jen-Chieh
    Hong, Ya-Chun
    Yang, Chun-Ming
    Mannathan, Subramaniyan
    Cheng, Chien-Hong
    ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (08): : 1615 - 1619