The tertiary sulfonamide as a latent directed-metalation group:: Ni0-catalyzed reductive cleavage and cross-coupling reactions of aryl sulfonamides with Grignard reagents

被引：47
|
作者：
Milburn, RR [1 ]
Snieckus, V [1 ]
机构：
[1] Queens Univ, Dept Chem, Kingston, ON K7L 3N6, Canada
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2004年 / 43卷 / 07期
关键词：
arenes; cross-coupling; magnesium; nickel; sulfonamides;
D O I：
10.1002/anie.200352633
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A mild method for the Ni0-catalyzed hydrodesulfamoylation (see scheme, B) of aryl sulfonamides (1→2) with iPr2Mg or iPrMgCl as β-hydride transfer sources can be linked with directed ortho metalation (A and C) to give meta-substituted aromatics 2. Cross-coupling process with alkyl and aryl Grignard reagents furnish disubstituted benzenes and bi- and teraryl compounds.
引用
收藏
页码：888 / 891
页数：4
相关论文
共 12 条
  • [1] Ni-Catalyzed Kumada-Corriu Cross-Coupling Reactions of Tertiary Grignard Reagents and Bromostyrenes
    Li, Kaidi
    Zu, Bing
    Mazet, Clement
    ORGANIC LETTERS, 2024, 26 (28) : 6047 - 6052
  • [2] Iron-Catalyzed Tandem Cyclization and Cross-Coupling Reactions of Iodoalkanes and Aryl Grignard Reagents
    Kim, Jae Gon
    Son, Young Hoon
    Seo, Jin Won
    Kang, Eun Joo
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (08) : 1781 - 1789
  • [3] Iron-Catalyzed Enantioselective Cross-Coupling Reactions of α-Chloroesters with Aryl Grignard Reagents
    Jin, Masayoshi
    Adak, Laksmikanta
    Nakamura, Masaharu
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (22) : 7128 - 7134
  • [4] Chemoselective Chromium(II)-Catalyzed Cross-Coupling Reactions of Dichlorinated Heteroaromatics with Functionalized Aryl Grignard Reagents
    Steib, Andreas K.
    Kuzmina, Olesya M.
    Fernandez, Sarah
    Malhotra, Sushant
    Knochel, Paul
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (05) : 1961 - 1965
  • [5] 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
  • [6] Iron-catalyzed cross-coupling reactions of alkyl-grignard reagents with aryl chlorides, tosylates, and triflates
    Fürstner, A
    Leitner, A
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2002, 41 (04) : 609 - +
  • [7] Nickel-Catalyzed Cross-Coupling of Aryl Bromides with Tertiary Grignard Reagents Utilizing Donor-Functionalized N-Heterocyclic Carbenes (NHCs)
    Lohre, Claudia
    Droege, Thomas
    Wang, Congyang
    Glorius, Frank
    CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (22) : 6052 - 6055
  • [8] Synthesis of α-trifluoromethylstyrene derivatives via Ni-catalyzed cross-coupling of 2-bromo-3,3,3-trifluoropropene and aryl Grignard reagents
    Kobayashi, Osamu
    Uraguchi, Daisuke
    Yamakawa, Tetsu
    JOURNAL OF FLUORINE CHEMISTRY, 2009, 130 (06) : 591 - 594
  • [9] A Practical Procedure for Iron-Catalyzed Cross-Coupling Reactions of Sterically Hindered Aryl-Grignard Reagents with Primary Alkyl Halides
    Sun, Chang-Liang
    Krause, Helga
    Fuerstner, Alois
    ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (06) : 1281 - 1291
  • [10] Mechanistic Insight into Rh-Catalyzed C(sp2)-O Bond Cleavage Applied to Cross-Coupling Reaction of Benzofurans with Aryl Grignard Reagents
    Iwasaki, Takanori
    Ishiga, Wataru
    Pal, Shrinwantu
    Nozaki, Kyoko
    Kambe, Nobuaki
    ACS CATALYSIS, 2022, 12 (13) : 7936 - 7949
12