Nickel-catalyzed cross-coupling reaction of alkyl halides with organozinc and Grignard reagents with 1,3,8,10-tetraenes as additives

被引：113
|
作者：
Terao, J
Todo, H
Watanabe, H
Ikumi, A
Kambe, N
机构：
[1] Osaka Univ, Dept Mol Chem & Sci, Grad Sch Engn, Suita, Osaka 5650871, Japan
[2] Osaka Univ, Technol Ctr Atoms Mol & Ions Control, Grad Sch Engn, Suita, Osaka 5650871, Japan
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2004年 / 43卷 / 45期
关键词：
alkyl halides; cross-coupling; Grignard reagents; nickel; organozinc reagents;
D O I：
10.1002/anie.200460246
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Essential additives: The addition of bis(1,3-butadienyl) compounds (tetraenes) was essential in the efficient Nicatalyzed cross-coupling of organozinc reagents with alkyl bromides and a tosylate (see scheme, X = C(CO2Me)2 or NCH2Ph). The efficiency of the Ni-catalyzed cross-coupling of an alkyl fluoride with a Grignard reagent was also improved by using these tetraenes.
引用
收藏
页码：6180 / 6182
页数：3
相关论文
共 50 条
  • [21] Nickel-catalyzed cross-coupling of bromophenols with Grignard reagents in the solid phase synthesis
    Heon Park
    Sang-Il Yoon
    Kwangyong Park
    Yoon-Sik Lee
    Molecular Diversity, 2000, 5 : 57 - 60
  • [22] Cross-Coupling of Nonactivated Alkyl Halides with Alkynyl Grignard Reagents: A Nickel Pincer Complex as the Catalyst
    Vechorkin, Oleg
    Godinat, Aurelien
    Scopelliti, Rosario
    Hu, Xile
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (49) : 11777 - 11781
  • [23] Nickel-Catalyzed Negishi Cross-Coupling of Alkyl Halides, Including Unactivated Tertiary Halides, with a Boron-Stabilized Organozinc Reagent
    Guo, Panchi
    Jin, Hao
    Han, Jinhui
    Xu, Liang
    Li, Pengfei
    Zhan, Miao
    ORGANIC LETTERS, 2023, : 1268 - 1273
  • [24] Preparation of Functionalized Aryl Iron(II) Compounds and a Nickel-Catalyzed Cross-Coupling with Alkyl Halides
    Wunderlich, Stefan H.
    Knochel, Paid
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (51) : 9717 - 9720
  • [25] Nickel-Catalyzed Reductive Cross-Coupling of Aryl Halides
    Qian, Qun
    Zang, Zhenhua
    Wang, Shulin
    Chen, Yang
    Lin, Kunhua
    Gong, Hegui
    SYNLETT, 2013, 24 (05) : 619 - 624
  • [26] Nickel-catalyzed cross-coupling of sterically hindered 1-bromomethyl-o-carborane with alkyl and aryl Grignard reagents
    Lu, Juyou
    Wan, Hong
    Xue, Yunna
    Du, Yongmei
    Lu, Jian
    TETRAHEDRON, 2015, 71 (41) : 7842 - 7846
  • [27] Nickel-Catalyzed Alkenylative Cross-Coupling Reaction of Alkyl Sulfides
    Ishizuka, Kentaro
    Seike, Hirofumi
    Hatakeyama, Takuji
    Nakamura, Masaharu
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (38) : 13117 - 13119
  • [28] Nickel-Catalyzed Cross-Coupling of Bromodifluoromethylphosphonates with Arylboron Reagents
    Kuriyama, Masami
    Maeda, Genki
    Kamata, Kazuya
    Kodama, Yusuke
    Yamamoto, Kosuke
    Onomura, Osamu
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (01) : 116 - 121
  • [29] The Cobalt-catalyzing Cross-Coupling Reaction of Alkyl Halides with Alkyl Grignard Reagents: A New Route to Constructing Quaternary Carbon Centers
    Iwasaki, Takanori
    Takagawa, Hiroaki
    Okamoto, Kanako
    Singh, Surya Prakash
    Kuniyasu, Hitoshi
    Kambe, Nobuaki
    SYNTHESIS-STUTTGART, 2014, 46 (12): : 1583 - 1592
  • [30] Direct Application of Phenolic Salts to Nickel-Catalyzed Cross-Coupling Reactions with Aryl Grignard Reagents
    Yu, Da-Gang
    Li, Bi-Jie
    Zheng, Shu-Fang
    Guan, Bing-Tao
    Wang, Bi-Qing
    Shi, Zhang-Jie
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (27) : 4566 - 4570
12345