Metal-catalyzed direct alkylations of (hetero)arenes via C-H bond cleavages with unactivated alkyl halides

被引:446
作者
Ackermann, Lutz [1 ]
机构
[1] Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
关键词
CROSS-COUPLING REACTIONS; DIRECT ARYLATION; ARYL CHLORIDES; DIRECT ALKYNYLATION; PHOSPHINE OXIDES; DIRECT FUNCTIONALIZATION; AROMATIC-COMPOUNDS; FORMING REACTIONS; BENZYL ALCOHOLS; PALLADIUM;
D O I
10.1039/c0cc00778a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Significant progress has been made in direct alkylations of (hetero)arenes with unactivated alkyl halides. Thus, C-H bond functionalizations were accomplished with beta-hydrogen-containing alkyl halides in the presence of palladium, nickel or ruthenium catalysts under basic reaction conditions. A valuable asset of these methodologies is represented by their excellent regio- and chemoselectivities, along with remarkable mild reaction conditions, rendering this approach an attractive alternative to traditional alkylation strategies.
引用
收藏
页码:4866 / 4877
页数:12
相关论文
共 180 条
  • [1] Catalytic arylation reactions by C-H bond activation with aryl tosylates
    Ackermann, L
    Althammer, A
    Born, R
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (16) : 2619 - 2622
  • [2] Air-stable phosphine oxides as preligands for catalytic activation reactions of C-Cl, C-F, and C-H bonds
    Ackermann, L
    Born, R
    Spatz, JH
    Althammer, A
    Gschrei, CJ
    [J]. PURE AND APPLIED CHEMISTRY, 2006, 78 (02) : 209 - 214
  • [3] Phosphine oxides as preligands in ruthenium-catalyzed arylations via C-H bond functionalization using aryl chlorides
    Ackermann, L
    [J]. ORGANIC LETTERS, 2005, 7 (14) : 3123 - 3125
  • [4] Dehydrative Direct Arylations of Arenes with Phenols via Ruthenium-Catalyzed C-H and C-OH Bond Functionalizations
    Ackermann, Lutz
    Mulzer, Michael
    [J]. ORGANIC LETTERS, 2008, 10 (21) : 5043 - 5045
  • [5] Copper-catalyzed "click" reaction/direct arylation sequence: Modular syntheses of 1,2,3-triazoles
    Ackermann, Lutz
    Potukuchi, Harish K.
    Landsberg, Dirk
    Vicente, Ruben
    [J]. ORGANIC LETTERS, 2008, 10 (14) : 3081 - 3084
  • [6] [RuCl3(H2O)n]-catalyzed direct arylations
    Ackermann, Lutz
    Althammer, Andreas
    Born, Robert
    [J]. TETRAHEDRON, 2008, 64 (26) : 6115 - 6124
  • [7] Assisted ruthenium-catalyzed C-H bond activation: Carboxylic acids as cocatalysts for generally applicable direct arylations in apolar solvents
    Ackermann, Lutz
    Vicente, Ruben
    Althammer, Andreas
    [J]. ORGANIC LETTERS, 2008, 10 (11) : 2299 - 2302
  • [8] Palladium-catalyzed direct arylations of 1,2,3-triazoles with aryl chlorides using conventional heating
    Ackermann, Lutz
    Vicente, Ruben
    Born, Robert
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (05) : 741 - 748
  • [9] [RuCl3(H2O)n]-catalyzed direct arylations with bromides as electrophiles
    Ackermann, Lutz
    Althammer, Andreas
    Born, Robert
    [J]. SYNLETT, 2007, (18) : 2833 - 2836
  • [10] Ruthenium(IV) alkylidenes as precatalysts for direct arylations of Alkenes with aryl chlorides and an application to sequential catalysis
    Ackermann, Lutz
    Born, Robert
    Alvarez-Bercedo, Paula
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (33) : 6364 - 6367