Significantly improved method for the Pd-catalyzed coupling of phenols with aryl halides: Understanding ligand effects

被引:295
作者
Burgos, Carlos H. [1 ]
Barder, Timothy E. [1 ]
Huang, Xiaohua [1 ]
Buchwald, Stephen L. [1 ]
机构
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
关键词
biaryl phosphines; C-O bond formation; palladium; substituent effects; synthetic methods;
D O I
10.1002/anie.200601253
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) A variety of diaryl ethers were synthesized by the Pd-catalyzed reaction of (hetero)-aryl halides and phenols. These reactions were achieved through the use of two new di-tert-butylphosphino biaryl ligands that overcome several limitations of previously described methods. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:4321 / 4326
页数:6
相关论文
共 34 条
  • [1] Novel electron-rich bulky phosphine ligands facilitate the palladium-catalyzed preparation of diaryl ethers
    Aranyos, A
    Old, DW
    Kiyomori, A
    Wolfe, JP
    Sadighi, JP
    Buchwald, SL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (18) : 4369 - 4378
  • [2] New synthetic method of aromatic ethers under microwave irradiation in dry media.
    Bogdal, D
    Pielichowski, J
    Boron, A
    [J]. SYNTHETIC COMMUNICATIONS, 1998, 28 (16) : 3029 - 3039
  • [3] Ullmann diaryl ether synthesis: Rate acceleration by 2,2,6,6-tetramethylheptane-3,5-dione
    Buck, E
    Song, ZJ
    Tschaen, D
    Dormer, PG
    Volante, RP
    Reider, PJ
    [J]. ORGANIC LETTERS, 2002, 4 (09) : 1623 - 1626
  • [4] Mild Ullmann-type biaryl ether formation reaction by combination of ortho-substituent and ligand effects
    Cai, Q
    Zou, BL
    Ma, DW
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (08) : 1276 - 1279
  • [5] Cai Q., 2006, ANGEW CHEM, V118, P1298
  • [6] Copper promoted C-N and C-O bond cross-coupling with phenyl and pyridylboronates
    Chan, DMT
    Monaco, KL
    Li, RH
    Bonne, D
    Clark, CG
    Lam, PYS
    [J]. TETRAHEDRON LETTERS, 2003, 44 (19) : 3863 - 3865
  • [7] New N- and O-arylations with phenylboronic acids and cupric acetate
    Chan, DMT
    Monaco, KL
    Wang, RP
    Winters, MP
    [J]. TETRAHEDRON LETTERS, 1998, 39 (19) : 2933 - 2936
  • [8] Chaouchi M, 2002, EUR J ORG CHEM, V2002, P1278
  • [9] Rapid and diverse route to natural product-like biaryl ether containing macrocycles
    Cristau, P
    Vors, JP
    Zhu, JP
    [J]. TETRAHEDRON, 2003, 59 (40) : 7859 - 7870
  • [10] Intramolecular O-arylation of phenols with phenylboronic acids: Application to the synthesis of macrocyclic metalloproteinase inhibitors
    Decicco, CP
    Song, Y
    Evans, DA
    [J]. ORGANIC LETTERS, 2001, 3 (07) : 1029 - 1032