Cross-coupling reactions by cooperative Pd/Cu or Ni/Cu catalysis based on the catalytic generation of organocopper nucleophiles

被引:26
作者
Semba, Kazuhiko [1 ]
Nakao, Yoshiaki [1 ]
机构
[1] Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Nishikyo Ku, Kyoto 6158510, Japan
关键词
Cooperative catalysis; Cross-coupling; Palladium; Nickel; Copper; ANTI-MARKOVNIKOV OXIDATION; DUAL CATALYSIS; ENANTIOSELECTIVE ARYLBORATION; STEREOSELECTIVE-SYNTHESIS; SONOGASHIRA REACTIONS; ALKYNYLZINC REAGENTS; SELECTIVE SYNTHESIS; ALLYLIC ALKYLATION; INTERNAL ALKYNES; ROOM-TEMPERATURE;
D O I
10.1016/j.tet.2018.12.013
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In this review, cross-coupling reactions by cooperative Pd/Cu or Ni/Cu catalysis based on catalytically generated organocopper nucleophiles are summarized. Compared to conventional methods based on the use of stoichiometric amounts of pre-synthesized organometallic reagents, these methods are powerful tools for the alkynylation, arylation, alkenylation, and alkylation of organic electrophiles, especially as they can be carried out in a highly step-economical manner with readily available starting materials based on simple arenes, carboxylic acids, alkenes, and alkynes as pre-nucleophiles. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码:709 / 719
页数:11
相关论文
共 105 条
[1]   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
[2]  
[Anonymous], 2002, CROSS COUPLING REACT
[3]   The nickel-catalyzed Sonogashira-Hagihara reaction [J].
Beletskaya, IP ;
Latyshev, GV ;
Tsvetkov, AV ;
Lukashev, NV .
TETRAHEDRON LETTERS, 2003, 44 (27) :5011-5013
[4]   PREPARATION AND CRYSTALLOGRAPHIC CHARACTERIZATION OF A HEXAMERIC TRIPHENYLPHOSPHINECOPPER HYDRIDE CLUSTER [J].
BEZMAN, SA ;
CHURCHIL.MR ;
OSBORN, JA ;
WORMALD, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (08) :2063-&
[5]   Modular Synthesis of Enantioenriched 1,1,2-Triarylethanes by an Enantioselective Arylboration and Cross-Coupling Sequence [J].
Chen, Bin ;
Cao, Peng ;
Yin, Xuemei ;
Liao, Yang ;
Jiang, Liyin ;
Ye, Jialin ;
Wang, Min ;
Liao, Jian .
ACS CATALYSIS, 2017, 7 (04) :2425-2429
[6]  
COREY EJ, 1972, TETRAHEDRON LETT, P3769
[7]  
Corriu R.J.P., 1972, J CHEM SOC CHEM COMM, V144
[8]   Palladium-Catalyzed Cross-Coupling Reactions of Organosilanols and Their Salts: Practical Alternatives to Boron- and Tin-Based Methods [J].
Denmark, Scott E. ;
Regen, Christopher S. .
ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (11) :1486-1499
[9]   Palladium-Catalyzed anti-Markovnikov Oxidation of Terminal Alkenes [J].
Dong, Jia Jia ;
Browne, Wesley R. ;
Feringa, Ben L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (03) :734-744
[10]   The first applications of carbene ligands in cross-couplings of alkyl electrophiles: Sonogashira reactions of unactivated alkyl bromides and iodides [J].
Eckhardt, M ;
Fu, GC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (45) :13642-13643