Miyaura Borylation and One-Pot Two-Step Homocoupling of Aryl Chlorides and Bromides under Solvent-Free Conditions

被引：54
作者：
Dzhevakov, Pavel B. [1 ]
Topchiy, Maxim A. [1 ]
Zharkova, Daria A. [2 ]
Morozov, Oleg S. [1 ]
Asachenko, Andrey F. [1 ]
Nechaev, Mikhail S. [1 ,2 ]
机构：
[1] Russian Acad Sci, AV Topchiev Petrochem Synth Inst, Moscow 119991, Russia
[2] Moscow MV Lomonosov State Univ, Moscow 119991, Russia
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2016年 / 358卷 / 06期
关键词：
cross-coupling reactions; homocoupling; Miyaura borylation; palladium; solvent-free reactions; CROSS-COUPLING REACTION; PALLADIUM-CATALYZED BORYLATION; ORGANIC-SYNTHESIS; HALIDES; MICROWAVE;
D O I：
10.1002/adsc.201500844
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
Solvent-free protocols for Miyaura borylation and the one-pot, two-step homocoupling of aryl halides are reported for the first time. Bis(di-benzylideneacetone) palladium(0) [Pd(dba)(2)] is an optimal source of palladium for Miyaura borylation, while for one-pot two-step homocoupling palladium(II) acetate [Pd(OAc)(2)] gives highest yields. Aryl bromides are coupled most efficiently using the DPEphos ligand. Chlorides are coupled using XPhos. The developed protocols are robust, versatile and easily reproducible on a large scale.
引用
收藏
页码：977 / 983
页数：7
相关论文
共 37 条
  • [1] Development of new methods in modern selective organic synthesis: preparation of functionalized molecules with atomic precision
    Ananikov, V. P.
    Khemchyan, L. L.
    Ivanova, Yu V.
    Bukhtiyarov, V. I.
    Sorokin, A. M.
    Prosvirin, I. P.
    Vatsadze, S. Z.
    Medved'ko, A. V.
    Nuriev, V. N.
    Dilman, A. D.
    Levin, V. V.
    Koptyug, I. V.
    Kovtunov, K. V.
    Zhivonitko, V. V.
    Likholobov, V. A.
    Romanenko, A. V.
    Simonov, P. A.
    Nenajdenko, V. G.
    Shmatova, I.
    Muzalevskiy, V. M.
    Nechaev, M. S.
    Asachenko, A. F.
    Morozov, S.
    Dzhevakov, P. B.
    Osipov, S. N.
    Vorobyeva, D. V.
    Topchiy, M. A.
    Zotova, M. A.
    Ponomarenko, S. A.
    Borshchev, V.
    Luponosov, Yu N.
    Rempel, A. A.
    Valeeva, A. A.
    Stakheev, A. Yu.
    Turov, V.
    Mashkovsky, I. S.
    Sysolyatin, S. V.
    Malykhin, V. V.
    Bukhtiyarova, G. A.
    Terent'ev, A. O.
    Krylov, I. B.
    [J]. RUSSIAN CHEMICAL REVIEWS, 2014, 83 (10) : 885 - 985
  • [2] Green Chemistry: Principles and Practice
    Anastas, Paul
    Eghbali, Nicolas
    [J]. CHEMICAL SOCIETY REVIEWS, 2010, 39 (01) : 301 - 312
  • [3] Suzuki-Miyaura Cross-Coupling under Solvent-Free Conditions
    Asachenko, Andrey F.
    Sorochkina, Kristina R.
    Dzhevakov, Pavel B.
    Topchiy, Maxim A.
    Nechaev, Mikhail S.
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (18) : 3553 - 3557
  • [4] Billingsley K.L., 2007, ANGEW CHEMIE, V119, P5455
  • [5] An improved system for the palladium-catalyzed borylation of aryl halides with pinacol borane
    Billingsley, Kelvin L.
    Buchwald, Stephen L.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (14) : 5589 - 5591
  • [6] 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
  • [7] Organocatalytic reactions: effects of ball milling, microwave and ultrasound irradiation
    Bruckmann, Angelika
    Krebs, Anke
    Bolm, Carsten
    [J]. GREEN CHEMISTRY, 2008, 10 (11) : 1131 - 1141
  • [8] Recent advances in solventless organic reactions: towards benign synthesis with remarkable versatility
    Cave, GWV
    Raston, CL
    Scott, JL
    [J]. CHEMICAL COMMUNICATIONS, 2001, (21) : 2159 - 2169
  • [9] A decade advancement of transition metal-catalyzed borylation of aryl halides and sulfonates
    Chow, Wing Kin
    Yuen, On Ying
    Choy, Pui Ying
    So, Chau Ming
    Lau, Chak Po
    Wong, Wing Tak
    Kwong, Fuk Yee
    [J]. RSC ADVANCES, 2013, 3 (31): : 12518 - 12539
  • [10] Carbon-Boron Bond Cross-Coupling Reaction Catalyzed by -PPh2 Containing Palladium-Indolylphosphine Complexes
    Chow, Wing Kin
    Yuen, On Ying
    So, Chau Ming
    Wong, Wing Tak
    Kwong, Fuk Yee
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (07) : 3543 - 3548
1234