N-(Hetero)arylations with Metalated (Hetero)aryls: Recent Advances in First-Row Transition-Metal-Mediated Cross-Couplings

被引：17
作者：
Ribaucourt, Aubert [1 ]
Cossy, Janine [1 ]
机构：
[1] PSL Univ, Mol Macromol Chem & Mat C3M, ESPCI Paris, CNRS, F-75005 Paris, France
来源：
ACS CATALYSIS | 2020年 / 10卷 / 17期
关键词：
amination; cross-coupling; nonprecious metal; umpolung; oxidative amination; CATALYZED ELECTROPHILIC AMINATION; C-N; ARYL BROMIDES; BORONIC ACIDS; POLYFUNCTIONAL ARYL; ARYLBORONIC ACIDS; TERTIARY-AMINES; COPPER; PALLADIUM; ARYLATION;
D O I：
10.1021/acscatal.0c02805
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
Transition-metal-catalyzed C(sp(2))-N bond forming reactions represent a very active field of research in chemistry. This review outlines the recent developments of the first-row transition-metal-catalyzed non-Buchwald-Hartwig cross-couplings (i.e., not taking place between a (hetero)aryl (pseudo)halide and an amine or other nitrogen-containing derivatives). The oxidative and umpolung cross-couplings represent the two main types of transformations discussed in this review.
引用
收藏
页码：10127 / 10148
页数：22
相关论文
共 95 条
  • [1] Reaction of Nitrogen-Radicals with Organometallics Under Ni-Catalysis: N-Arylations and Amino-Functionalization Cascades
    Angelina, Lucrezia
    Davies, Jacob
    Simonetti, Marco
    Sanz, Laia Malet
    Sheikh, Nadeem S.
    Leonori, Daniele
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (15) : 5003 - 5007
  • [2] Ligand-Free Iron-Catalyzed C-F Amination of Diarylamines: A One-Pot Regioselective Synthesis of Diaryl Dihydrophenazines
    Aoki, Yuma
    O'Brien, Harry M.
    Kawasaki, Hiroto
    Takaya, Hikaru
    Nakamura, Masaharu
    [J]. ORGANIC LETTERS, 2019, 21 (02) : 461 - 464
  • [3] Copper-Catalyzed Electrophilic Amidation of Organotrifluoroborates with Use of N-Methoxyamides
    Banjo, Shona
    Nakasuji, Eiko
    Meguro, Tatsuhiko
    Sato, Takaaki
    Chida, Noritaka
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (33) : 7941 - 7947
  • [4] Developments in Transition-Metal-Catalyzed Reactions Using Electrophilic Nitrogen Sources
    Barker, Timothy J.
    Jarvo, Elizabeth R.
    [J]. SYNTHESIS-STUTTGART, 2011, (24): : 3954 - 3964
  • [5] Titanium-Mediated Amination of Grignard Reagents Using Primary and Secondary Amines
    Barker, Timothy J.
    Jarvo, Elizabeth R.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (36) : 8325 - 8328
  • [6] Umpolung Amination: Nickel-Catalyzed Coupling Reactions of N,N-Dialkyl-N-chloroamines with Diorganozinc Reagents
    Barker, Timothy J.
    Jarvo, Elizabeth R.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (43) : 15598 - +
  • [7] The Complementary Competitors: Palladium and Copper in C-N Cross-Coupling Reactions
    Beletskaya, Irina P.
    Cheprakov, Andrei V.
    [J]. ORGANOMETALLICS, 2012, 31 (22) : 7753 - 7808
  • [8] Copper-catalyzed electrophilic amination of organozinc nucleophiles:: Documentation of O-benzoyl hydroxylamines as broadly useful R2N(+) and RHN(+) synthons
    Berman, AM
    Johnson, JS
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (01) : 219 - 224
  • [9] Nickel-catalyzed electrophilic amination of organozinc halides
    Berman, AM
    Johnson, JS
    [J]. SYNLETT, 2005, (11) : 1799 - 1801
  • [10] Copper-catalyzed electrophilic amination of functionalized diarylzinc reagents
    Berman, AM
    Johnson, JS
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (01) : 364 - 366
12345678910