Synthesis of Multisubstituted Allylic Alcohols via a Nickel-Catalyzed Cross-Electrophile Ring-Opening Reaction

被引:8
|
作者
Hu, Weitao [1 ]
Lin, Zhiyang [1 ]
Wang, Chuan [1 ,2 ]
机构
[1] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China
[2] Chinese Acad Sci, Ctr Excellence Mol Synth, Hefei 230026, Anhui, Peoples R China
基金
中国国家自然科学基金;
关键词
STEREOSELECTIVE-SYNTHESIS; BIOLOGICAL EVALUATION; COUPLING REACTIONS; GROWTH-INHIBITION; VINYL EPOXIDES; HALIDES; TAMOXIFEN; DERIVATIVES; ALDEHYDES; VIOXX(R);
D O I
10.1021/acs.orglett.2c02199
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein we report a nickel-catalyzed cross-electrophile ring-opening reaction of vinyl epoxides wherein aryl iodides, alkyl iodides, and benzyl chlorides can all serve as the electrophilic coupling partners, providing a new approach to preparing multisubstituted allylic alcohols. This new method features broad substrate scope (76 examples), good step-economy, and high L/B-and E/Z selectivity as well as mild reaction conditions.
引用
收藏
页码:5751 / 5755
页数:5
相关论文
共 50 条
  • [21] Nickel-Catalyzed Cross-Electrophile Coupling of the Difluoromethyl Group for Fluorinated Cyclopropane Synthesis
    Lucas, Erika L.
    McGinnis, Tristan M.
    Castro, Anthony J.
    Jarvo, Elizabeth R.
    SYNLETT, 2021, 32 (15) : 1525 - 1530
  • [22] Nickel-catalyzed cross-electrophile coupling reactions of vinyl halides
    Johnson, Keywan
    Weix, Daniel
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 250
  • [23] Nickel-catalyzed cross-electrophile coupling reactions of diol derivatives
    Sanford, Amberly
    Thane, Taylor
    Jarvo, Elizabeth
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 258
  • [24] Nickel-catalyzed stereospecific reductive cross-electrophile coupling reactions
    Jarvo, Elizabeth
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 254
  • [25] Nickel-Catalyzed Asymmetric Cross-Electrophile trans-Aryl- Benzylation of α-Naphthyl Propargylic Alcohols
    Lin, Zhiyang
    Hu, Weitao
    Zhang, Linchuan
    Wang, Chuan
    ACS CATALYSIS, 2023, 13 (10) : 6795 - 6803
  • [26] Nickel-Catalyzed Ring-Opening Allylation of Cyclopropanols via Homoenolate
    Sekiguchi, Yoshiya
    Lee, Yan Ying
    Yoshikai, Naohiko
    ORGANIC LETTERS, 2021, 23 (15) : 5993 - 5997
  • [27] Nickel-Catalyzed Cross-Electrophile Coupling Reactions between Allylic Acetates and gem-Difluorovinyl Tosylate
    He, Xiaochun
    Liu, Jiangjun
    Chen, Gang
    Xiong, Baojian
    Xiao, Xue
    Chen, Lei
    Zhang, Xuemei
    Dong, Lin
    Ma, Xuelei
    Lian, Zhong
    ORGANIC LETTERS, 2022, 24 (19) : 3538 - 3543
  • [28] Nickel-catalyzed, stereospecific, intramolecular, reductive cross-electrophile coupling of allylic and benzylic ethers with alkyl halides
    Erickson, Lucas
    Tollefson, Emily
    Lucas, Erika
    Jarvo, Elizabeth
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 251
  • [29] Nickel-catalyzed reductive cross-electrophile coupling reactions of alkyl fluorides for cyclopropane synthesis
    Lucas, Erika
    Erickson, Lucas
    Tollefson, Emily
    Jarvo, Elizabeth
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 254
  • [30] Nickel-Catalyzed Borylative Ring-Opening Reaction of Vinylcyclopropanes with Bis(pinacolato)diboron Yielding Allylic Boronates
    Sumida, Yuto
    Yorimitsu, Hideki
    Oshima, Koichiro
    ORGANIC LETTERS, 2008, 10 (20) : 4677 - 4679