Biphenylene-substituted ruthenocenylphosphine for Suzuki-Miyaura coupling of aryl chlorides

被引:58
作者
Hoshi, Takashi [1 ]
Nakazawa, Taichi [2 ]
Saitoh, Ippei [2 ]
Mori, Ayako [1 ]
Suzuki, Toshio [1 ]
Sakai, Jun-ichi [1 ]
Hagiwara, Hisahiro [2 ]
机构
[1] Niigata Univ, Fac Engn, Niigata 9502181, Japan
[2] Niigata Univ, Grad Sch Sci & Technol, Nishi Ku, Niigata 9502181, Japan
关键词
D O I
10.1021/ol800567q
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
High activity in the palladium-catalyzed Suzuki-Miyaura reactions of aryl chlorides with arylboronic acids was furnished using biphenylene-substituted di-tert-butylruthenocenylphosphine (R-Phos) as a supporting ligand. Substrate combinations even for the construction of highly hindered tetra- ortho-substituted biaryls can be achieved in good to excellent yields with low catalyst loadings in short reaction times.
引用
收藏
页码:2063 / 2066
页数:4
相关论文
共 56 条
  • [21] Pd-catalyzed amidations of aryl chlorides using monodentate biaryl phosphine ligands: A kinetic, computational, and synthetic investigation
    Ikawa, Takashi
    Barder, Timothy E.
    Biscoe, Mark R.
    Buchwald, Stephen L.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (43) : 13001 - 13007
  • [22] Phosphines having a 2,3,4,5-tetraphenylphenyl moiety: Effective ligands in palladium-catalyzed transformations of aryl chlorides
    Iwasawa, Tetsuo
    Komano, Tomoko
    Tajima, Atsunori
    Tokunaga, Makoto
    Obora, Yasushi
    Fujihara, Tetsuaki
    Tsuji, Yasushi
    [J]. ORGANOMETALLICS, 2006, 25 (19) : 4665 - 4669
  • [23] New air-stable planar chiral ferrocenyl monophosphine ligands: Suzuki cross-coupling of aryl chlorides and bromides
    Jensen, JF
    Johannsen, M
    [J]. ORGANIC LETTERS, 2003, 5 (17) : 3025 - 3028
  • [24] Air stable, sterically hindered ferrocenyl dialkylphosphines for palladium-catalyzed C-C, C-N, and C-O bond-forming cross-couplings
    Kataoka, N
    Shelby, Q
    Stambuli, JP
    Hartwig, JF
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (16) : 5553 - 5566
  • [25] Palladium(II) complexes of 2-dimethylamino-2′-diphenylphosphino-1,1′-binaphthyl (MAP) with unique P,Cσ-coordination and their catalytic activity in allylic substitution, Hartwig-Buchwald amination, and Suzuki coupling
    Kocovsky, P
    Vyskocil, S
    Císarová, I
    Sejbal, J
    Tislerová, I
    Smrcina, M
    Lloyd-Jones, GC
    Stephen, SC
    Butts, CP
    Murray, M
    Langer, V
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (33) : 7714 - 7715
  • [26] Recent applications of the Suzuki-Miyaura cross-coupling reaction in organic synthesis
    Kotha, S
    Lahiri, K
    Kashinath, D
    [J]. TETRAHEDRON, 2002, 58 (48) : 9633 - 9695
  • [27] An active ferrocenyl triarylphosphine for palladium-catalyzed Suzuki-Miyaura cross-coupling of aryl halides
    Kwong, FY
    Chan, KS
    Yeung, CH
    Chan, ASC
    [J]. CHEMICAL COMMUNICATIONS, 2004, (20) : 2336 - 2337
  • [28] Versatile catalysts for the Suzuki cross-coupling of arylboronic acids with aryl and vinyl halides and triflates under mild conditions
    Littke, AF
    Dai, CY
    Fu, GC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (17) : 4020 - 4028
  • [29] Littke AF, 2002, ANGEW CHEM INT EDIT, V41, P4176, DOI 10.1002/1521-3773(20021115)41:22<4176::AID-ANIE4176>3.0.CO
  • [30] 2-U