Enantioselective Radical Addition/Cross-Coupling of Organozinc Reagents, Alkyl Iodides, and Alkenyl Boron Reagents

被引:101
|
作者
Chierchia, Matteo [1 ]
Xu, Peilin [1 ]
Lovinger, Gabriel J. [1 ]
Morken, James P. [1 ]
机构
[1] Boston Coll, Dept Chem, 2609 Beacon St, Chestnut Hill, MA 02467 USA
关键词
boron; catalysis; cross-coupling; nickel; radical reactions; CATALYZED INTERMOLECULAR TRIFLUOROMETHYLARYLATION; POLAR CROSSOVER REACTIONS; REDUCTIVE DICARBOFUNCTIONALIZATION; UNACTIVATED OLEFINS; HALIDES; CYCLIZATION; STYRENES; ESTERS; 1,2-DIFUNCTIONALIZATION; DIFUNCTIONALIZATION;
D O I
10.1002/anie.201908029
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A hybrid transition-metal/radical process is described that results in the addition of organozinc reagents and alkyl halides across alkenyl boron reagents in an enantioselective catalytic fashion. The reaction can be accomplished both intermolecularly and intramolecularly, providing useful product yields and high enantioselectivities in both manifolds.
引用
收藏
页码:14245 / 14249
页数:5
相关论文
共 50 条
  • [1] Nickel-Catalyzed Cross-Coupling of Aryltrimethylammonium Iodides with Organozinc Reagents
    Xie, Lan-Gui
    Wang, Zhong-Xia
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (21) : 4901 - 4904
  • [2] Generation and Cross-Coupling of Organozinc Reagents in Flow
    Herath, Ananda
    Molteni, Valentina
    Pan, Shifeng
    Loren, Jon
    ORGANIC LETTERS, 2018, 20 (23) : 7429 - 7432
  • [3] Enantioconvergent Fukuyama Cross-Coupling of Racemic Benzylic Organozinc Reagents
    Oost, Rik
    Misale, Antonio
    Maulide, Nuno
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (14) : 4587 - 4590
  • [4] Iron-Catalyzed Cross-Coupling Reactions of Alkyl Grignard Reagents with Alkenyl Carbonate
    Qin, Hongjian
    Yang, Xingbang
    Mintah Bonku, Emmanuel
    Zhu, Fuqiang
    Abduahadi, Safomuddin
    Yang, Peng
    Shen, Jingshan
    Akber Aisa, Haji
    ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (24) : 5026 - 5032
  • [5] STEREOSPECIFIC SYNTHESIS OF POLYFUNCTIONAL ALKENES BY THE CROSS-COUPLING OF FUNCTIONALIZED ZINC-COPPER REAGENTS WITH ALKENYL IODIDES
    MARQUAIS, S
    CAHIEZ, G
    KNOCHEL, P
    SYNLETT, 1994, (10) : 849 - 850
  • [6] Nickel-Catalyzed Cross-Coupling of Aryl Fluorides and Organozinc Reagents
    Zhu, Feng
    Wang, Zhong-Xia
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (10) : 4285 - 4292
  • [7] A Mild Negishi Cross-Coupling of 2-Heterocyclic Organozinc Reagents and Aryl Chlorides
    Luzung, Michael R.
    Patel, Jigar S.
    Yin, Jingjun
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (23) : 8330 - 8332
  • [8] Iron-Catalyzed Cross-Coupling of Alkyl Sulfonates with Arylzinc Reagents
    Ito, Shingo
    Fujiwara, Yu-ichi
    Nakamura, Eiichi
    Nakamura, Masaharu
    ORGANIC LETTERS, 2009, 11 (19) : 4306 - 4309
  • [9] Cobalt-Catalyzed Negishi Cross-Coupling Reactions of (Hetero)Arylzinc Reagents with Primary and Secondary Alkyl Bromides and Iodides
    Hammann, Jeffrey M.
    Haas, Diana
    Knochel, Paul
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (15) : 4478 - 4481
  • [10] Cross-Coupling of N-Allylic Sulfonimides with Organozinc Reagents at Room Temperature
    Tang, Xiang-Ling
    Wu, Zhao
    Li, Man-Bo
    Gu, Yonghong
    Tian, Shi-Kai
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (22) : 4107 - 4109