Mild and general conditions for the cross-coupling of aryl halides with pentafluorobenzene and other perfluoroaromatics

被引:192
作者
Lafrance, Marc [1 ]
Shore, Daniel [1 ]
Fagnou, Keith [1 ]
机构
[1] Univ Ottawa, Dept Chem, Ctr Catalysis Res & Innovat, Ottawa, ON K1N 6N5, Canada
关键词
PALLADIUM-CATALYZED ARYLATION; C-H ACTIVATION; LIQUID-CRYSTALLINE; EFFICIENT; DISCOVERY;
D O I
10.1021/ol0619967
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
New reaction conditions are described that enable the direct arylation of pentafluorobenzene with sterically encumbered aryl bromides and aryl chlorides. These reactions occur in high yield and under mild conditions. Notably, the reactions can be performed at 80 C in isopropyl acetate with a catalyst generated by the in situ mixing of Pd(OAc)(2) and S-Phos. The enhanced scope of these transformations should further reduce the need to use pentafluorophenylboronic acid in the construction of perfluoroarenes.
引用
收藏
页码:5097 / 5100
页数:4
相关论文
共 39 条
  • [1] The catalytic intermolecular orthoarylation of phenols
    Bedford, RB
    Coles, SJ
    Hursthouse, MB
    Limmert, ME
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (01) : 112 - 114
  • [2] Catalytic direct arylation with aryl chlorides, bromides, and iodides: Intramolecular studies leading to new intermolecular reactions
    Campeau, LC
    Parisien, M
    Jean, A
    Fagnou, K
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (02) : 581 - 590
  • [3] Palladium-catalyzed direct arylation of simple arenes in synthesis of biaryl molecules
    Campeau, LC
    Fagnou, K
    [J]. CHEMICAL COMMUNICATIONS, 2006, (12) : 1253 - 1264
  • [4] A solution to the 2-pyridyl organometallic cross-coupling problem:: Regioselective catalytic direct arylation of pyridine N-oxides
    Campeau, LC
    Rousseaux, S
    Fagnou, K
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (51) : 18020 - 18021
  • [5] Biaryl synthesis via direct arylation: Establishment of an efficient catalyst for intramolecular processes
    Campeau, LC
    Parisien, M
    Leblanc, M
    Fagnou, K
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (30) : 9186 - 9187
  • [6] Anilide ortho-arylation by using C-H activation methodology
    Daugulis, O
    Zaitsev, VG
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (26) : 4046 - 4048
  • [7] Diederich, 2008, METAL CATALYZED CROS
  • [8] Polyfluoroorganoboron oxygen compounds, part 3. The palladium-catalysed cross-coupling reaction of lithium polyfluorophenyltrimethoxyborates with 4-fluoroiodobenzene
    Frohn, HJ
    Adonin, NY
    Bardin, VV
    Starichenko, VF
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 2003, 122 (02) : 195 - 199
  • [9] Highly efficient cross-coupling reactions with the perfluoroorganotrifluoroborate salts K [RFBF3] (RF=C6F5, CF2=CF)
    Frohn, HJ
    Adonin, NY
    Bardin, VV
    Starichenko, VF
    [J]. TETRAHEDRON LETTERS, 2002, 43 (45) : 8111 - 8114
  • [10] Proton abstraction mechanism for the palladium-catalyzed intramolecular arylation
    García-Cuadrado, D
    Braga, AAC
    Maseras, F
    Echavarren, AM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (04) : 1066 - 1067