Nickel-Catalyzed, Regio- and Enantioselective Benzylic Alkenylation of Olefins with Alkenyl Bromide

被引:74
|
作者
Liu, Jiandong [1 ]
Gong, Hegui [1 ]
Zhu, Shaolin [2 ]
机构
[1] Shanghai Univ, Sch Mat Sci & Engn, Ctr Supramol Chem & Catalysis, Dept Chem, Shanghai 200444, Peoples R China
[2] Nanjing Univ, Sch Chem & Chem Engn, State Key Lab Coordinat Chem, Jiangsu Key Lab Adv Organ Mat Chem & Biomed, Nanjing 210093, Peoples R China
关键词
alkenes; alkenylation; asymmetric catalysis; isomerization; nickel; LINEAR-SELECTIVE HYDROARYLATION; SECONDARY ALKYL ELECTROPHILES; COUPLING REACTIONS; CROSS-COUPLINGS; ISOMERIZATION-HYDROBORATION; REMOTE; HALIDES; FUNCTIONALIZATION; ARYLATION; VINYL;
D O I
10.1002/anie.202012614
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A NiH-catalyzed migratory hydroalkenylation reaction of olefins with alkenyl bromides has been developed, affording benzylic alkenylation products with high yields and excellent chemoselectivity. The mild conditions of the reaction preclude olefinic products from undergoing further isomerization or subsequent alkenylation. Catalytic enantioselective hydroalkenylation of styrenes was achieved by using a chiral bisoxazoline ligand.
引用
收藏
页码:4060 / 4064
页数:5
相关论文
共 50 条
  • [1] Nickel-Catalyzed Regio- and Enantioselective Hydrofluorination in Unactivated Alkenes
    Kim, Minseok
    Han, Seunghoon
    Hong, Sungwoo
    SYNLETT, 2025, 36 (02) : 97 - 102
  • [2] Nickel-Catalyzed Regio- and Enantioselective Hydroarylation of 1,3-Dienes with Indoles
    Cheng, Lei
    Li, Ming-Ming
    Li, Mao-Lin
    Xiao, Li-Jun
    Xie, Jian-Hua
    Zhou, Qi-Lin
    CCS CHEMISTRY, 2022, 4 (08): : 2612 - 2619
  • [3] Nickel-Catalyzed Regio- and Enantioselective Borylative Coupling of Terminal Alkenes with Alkyl Halides
    Wang Hepan
    Xu Tao
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2023, 43 (09) : 3328 - 3330
  • [4] Nickel-Catalyzed Regio- and Enantioselective Aminolysis of 3,4-Epoxy Alcohols
    Wang, Chuan
    Yamamoto, Hisashi
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (13) : 4308 - 4311
  • [5] Nickel-catalyzed regio- and stereoselective hydrocyanation of allene
    Amako, Yuka
    Arai, Shigeru
    Nishida, Atsushi
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 251
  • [6] Nickel-Catalyzed Regio- and Enantioselective Hydroamination of Unactivated Alkenes Using Carbonyl Directing Groups
    Lee, Changseok
    Kang, Hyung-Joon
    Seo, Huiyeong
    Hong, Sungwoo
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (20) : 9091 - 9100
  • [7] Regio- and enantioselective hydrofluorination of internal alkenes via nickel-catalyzed hydrogen atom transfer
    Chen, Fan
    Zhao, Xiaoyu
    Miao, Weihang
    Li, Yingying
    Yuan, Ye
    Chu, Lingling
    CHINESE CHEMICAL LETTERS, 2025, 36 (05)
  • [8] Synthesis of α-N-Heteroaryl Ketones by Nickel-Catalyzed Chemo-, Regio- and Enantioselective Carbonylation of Alkenes and N-Alkenyl Heteroarenes
    Chen, Xiao-Yi
    Yu, Qiong
    Shu, Wei
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2025,
  • [9] Nickel Catalyzed Regio- and Stereoselective Alkylboration of Endocyclic Olefins
    Yang Chao
    Qi Xiangbing
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2022, 42 (02) : 657 - 658
  • [10] Enantioselective nickel-catalyzed reductive dicarbofunctionalization of olefins
    Anthony, David
    Diao, Tianning
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 256