Transition-Metal-Catalyzed Cross-Coupling Reactions of Grignard Reagents

被引:28
作者
Juhasz, Kinga [1 ]
Magyar, Agnes [1 ]
Hell, Zoltan [1 ]
机构
[1] Budapest Univ Technol & Econ, Dept Organ Chem & Technol, Muegyet Rkp 3, H-1111 Budapest, Hungary
来源
SYNTHESIS-STUTTGART | 2021年 / 53卷 / 06期
关键词
transition metals; Grignard reagent; cross-coupling; organometallic reagent; organic halides; Kumada-Tamao-Corriu coupling; SECONDARY ALKYL-HALIDES; CARBON BOND FORMATION; NICKEL-INDUCED CONVERSION; ONE-STEP TRANSFORMATIONS; AMIDO PINCER COMPLEXES; ARYL CHLORIDES; ALKENYL HALIDES; SUBSTITUTED PYRIDINES; EFFICIENT SYNTHESIS; DIRECT ARYLATION;
D O I
10.1055/s-0040-1705986
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Transition-metal-catalyzed cross-coupling of organo-halides, ethers, sulfides, amines, and alcohols (and derivatives thereof) with Grignard reagents, known as the Kumada-Tamao-Corriu reaction, can be used to prepare important intermediates in the synthesis of numerous-biologically active compounds. The most frequently used transition metals are nickel, palladium, and iron, but there are several examples for cross-coupling reactions catalyzed by copper, cobalt, manganese, chromium, etc. salts and complexes. The aim of this review is to summarize the most important transition-metal-catalyzed cross-coupling reactions realized in the period 2000 to 2020.
引用
收藏
页码:983 / 1002
页数:20
相关论文
共 179 条
[1]   Cross-coupling reactions of aryl and vinyl chlorides catalyzed by a palladium complex derived from an air-stable H-phosphonate [J].
Ackermann, L ;
Gschrei, CJ ;
Althammer, A ;
Riederer, M .
CHEMICAL COMMUNICATIONS, 2006, (13) :1419-1421
[2]   Well-Defined Air-Stable Palladium HASPO Complexes for Efficient Kumada-Corriu Cross-Couplings of (Hetero)Aryl or Alkenyl Tosylates [J].
Ackermann, Lutz ;
Kapdi, Anant R. ;
Fenner, Sabine ;
Kornhaass, Christoph ;
Schulzke, Carola .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (10) :2965-2971
[3]   The first palladium-catalyzed Sonogashira coupling of unactivated secondary alkyl bromides [J].
Altenhoff, G ;
Würtz, S ;
Glorius, F .
TETRAHEDRON LETTERS, 2006, 47 (17) :2925-2928
[4]   Manganese-Catalyzed Cross-Coupling of Aryl Halides and Grignard Reagents by a Radical Mechanism [J].
Antonacci, Giuseppe ;
Ahlburg, Andreas ;
Fristrup, Peter ;
Norrby, Per-Ola ;
Madsen, Robert .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (32) :4758-4764
[5]   NOVEL STEREOSPECIFIC ALKENYL-ALKENYL CROSS-COUPLING BY A PALLADIUM-CATALYZED OR NICKEL-CATALYZED REACTION OF ALKENYLALANES WITH ALKENYL HALIDES [J].
BABA, S ;
NEGISHI, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (21) :6729-6731
[6]  
Barbier P., 1899, CR HEBD ACAD SCI, V128, P110
[7]   Iron-phosphine, -phosphite, -arsine, and -carbene catalysts for the coupling of primary and secondary 2 alkyl halides with aryl Grignard reagents [J].
Bedford, RB ;
Betham, M ;
Bruce, DW ;
Danopoulos, AA ;
Frost, RM ;
Hird, M .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (03) :1104-1110
[8]   Simple iron-amine catalysts for the cross-coupling of aryl Grignards with alkyl halides bearing β-hydrogens [J].
Bedford, RB ;
Bruce, DW ;
Frost, RM ;
Hird, M .
CHEMICAL COMMUNICATIONS, 2005, (33) :4161-4163
[9]   Chromium-Catalyzed Cross-Coupling Reactions of Alkylmagnesium Reagents with Halo-Quinolines and Activated Aryl Chlorides [J].
Bellan, Andreas B. ;
Kuzmina, Olesya M. ;
Vetsova, Violeta A. ;
Knochel, Paul .
SYNTHESIS-STUTTGART, 2017, 49 (01) :188-194
[10]   Iron-Catalyzed C(sp2)-C(sp3) Cross-Coupling of Aryl Chlorobenzoates with Alkyl Grignard Reagents [J].
Bisz, Elwira ;
Szostak, Michal .
MOLECULES, 2020, 25 (01)