Ligand Promoted meta-C-H Chlorination of Anilines and Phenols

被引:104
作者
Shi, Hang [1 ]
Wang, Peng [1 ]
Suzuki, Shin [1 ]
Farmer, Marcus E. [1 ]
Yu, Jin-Quan [1 ]
机构
[1] Scripps Res Inst, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USA
关键词
PALLADIUM-CATALYZED SYNTHESIS; CROSS-COUPLING REACTIONS; AMINO-ACID LIGANDS; BOND ACTIVATION; ARYL CHLORIDES; AROMATIC FUNCTIONALIZATION; ARYLATION; TEMPLATE; ALKYLATION; NORBORNENE;
D O I
10.1021/jacs.6b11055
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Pd-catalyzed meta-C-H chlorination of anilines and phenols is developed using norbornene as the mediator. Heterocycles, including indole, thiophene, and indazole, are tolerated. The identification of a new pyridone-based ligand is crucial for the success of this meta-C-H chlorination reaction. Subsequent diverse transformations of the chlorinated products demonstrate the versatility of meta-C-H chlorination.
引用
收藏
页码:14876 / 14879
页数:4
相关论文
共 51 条
  • [1] Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153J, 10.1021/cr300153j]
  • [2] Remote para-C-H Functionalization of Arenes by a D-Shaped Biphenyl Template-Based Assembly
    Bag, Sukdev
    Patra, Tuhin
    Modak, Atanu
    Deb, Arghya
    Maity, Soham
    Dutta, Uttam
    Dey, Aniruddha
    Kancherla, Rajesh
    Maji, Arun
    Hazra, Avijit
    Bera, Milan
    Maiti, Debabrata
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (37) : 11888 - 11891
  • [3] Catalysts for Suzuki-Miyaura coupling processes: Scope and studies of the effect of ligand structure
    Barder, TE
    Walker, SD
    Martinelli, JR
    Buchwald, SL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) : 4685 - 4696
  • [4] Palladium-catalyzed borylation of aryl chlorides: Scope, applications, and computational studies
    Billingsley, Kelvin L.
    Barder, Timothy E.
    Buchwald, Stephen L.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (28) : 5359 - 5363
  • [5] PALLADIUM-CATALYZED C-C BOND FORMATION INVOLVING AROMATIC C-H ACTIVATION .3. ASPECTS OF AROMATIC-SUBSTITUTION AND STRUCTURE OF 1-BROMO-3-[3-(2-METHYLENECYCLOHEX-5-EN-1-YL)BICYCLO[2.2.1]-HEPT-2-YL]-4-BICYCLO[2.2.1]HEPT-2-YLBENZENE
    BOCELLI, G
    CATELLANI, M
    CHIUSOLI, GP
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1985, 279 (1-2) : 225 - 232
  • [6] PALLADIUM-CATALYZED C-C BOND FORMATION INVOLVING AROMATIC C-H ACTIVATION - X-RAY STRUCTURE OF 5-NITRO-8-(2-[2.2.1]BICYCLOHEPTYL)-1,2,3,4,4A,8B-HEXAHYDRO-1,4-METHANOBIPHENYLENE
    BOCELLI, G
    CATELLANI, M
    CHIUSOLI, GP
    LAROCCA, S
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1984, 265 (01) : C9 - C11
  • [7] Catellani M, 2005, TOP ORGANOMETAL CHEM, V14, P21
  • [8] Catalytic multistep reactions via palladacycles
    Catellani, M
    [J]. SYNLETT, 2003, (03) : 298 - 313
  • [9] Catalytic Sequential Reactions Involving Palladacycle-Directed Aryl Coupling Steps
    Catellani, Marta
    Motti, Elena
    Della Ca, Nicola
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (11) : 1512 - 1522
  • [10] Palladium(II)-Catalyzed C-H Activation/C-C Cross-Coupling Reactions: Versatility and Practicality
    Chen, Xiao
    Engle, Keary M.
    Wang, Dong-Hui
    Yu, Jin-Quan
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) : 5094 - 5115