Aminocarbonylation of Aryl Tosylates to Carboxamides

被引:18
|
作者
Chung, Seungwon [1 ]
Sach, Neal [3 ]
Choi, Chulho [1 ]
Yang, Xiaojing [1 ]
Drozda, Susan E. [1 ]
Singer, Robert A. [2 ]
Wright, Stephen W. [1 ]
机构
[1] Pfizer Global Res & Dev, Biotherapeut Chem, Groton, CT 06340 USA
[2] Pfizer Global Res & Dev, Chem Res & Dev, Groton, CT 06340 USA
[3] Pfizer Global Res & Dev, Oncol Chem, La Jolla, CA 92121 USA
关键词
PALLADIUM-CATALYZED CARBONYLATION; CROSS-COUPLING REACTIONS; ARYLBORONIC ACIDS; MESYLATES; HALIDES; ALKOXY; ALKOXYCARBONYLATION; ARENESULFONATES; CHLORIDES; PHENOLS;
D O I
10.1021/acs.orglett.5b01283
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The palladium - catalyzed aminocarbonylation of aryl tosylates with amines is reported. Suitable conditions were identified by high throughput reaction screening and then further optimized. The substrate scope of the reaction with respect to the aryl tosylate component and the amine component are reported. Competitive aminolysis of the aryl tosylates to afford the amine toluenesulfonamides and the phenol was not observed.
引用
收藏
页码:2848 / 2851
页数:4
相关论文
共 50 条
  • [1] Synthesis of Ortho-alkoxy-aryl Carboxamides via Palladium-Catalyzed Aminocarbonylation
    Takacs, Attila
    Abreu, Artur R.
    Peixoto, Andreia F.
    Pereira, Mariette
    Kollar, Laszlo
    SYNTHETIC COMMUNICATIONS, 2009, 39 (09) : 1534 - 1548
  • [2] Palladium Catalyzed Alkoxy- and Aminocarbonylation of Vinyl Tosylates
    Reeves, Diana C.
    Rodriguez, Sonia
    Lee, Heewon
    Haddad, Nizar
    Krishnamurthy, Dhileepkumar
    Senanayake, Chris H.
    ORGANIC LETTERS, 2011, 13 (09) : 2495 - 2497
  • [3] Photoinduced Aminocarbonylation of Aryl Iodides
    Kawamoto, Takuji
    Sato, Aoi
    Ryu, Ilhyong
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (42) : 14764 - 14767
  • [4] Cobalt-Catalyzed Aminocarbonylation of Alkyl Tosylates: Stereospecific Synthesis of Amides
    Sargent, Brendon T.
    Alexanian, Erik J.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (28) : 9533 - 9536
  • [5] Oxidative addition of aryl tosylates to palladium(0) and coupling of unactivated aryl tosylates at room temperature
    Roy, AH
    Hartwig, JF
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (29) : 8704 - 8705
  • [6] Highly Selective Synthesis of Carboxamides via Transition Metal Catalysed Aminocarbonylation
    Kiss, Mercedesz
    Takacs, Attila
    Kollar, Laszlo
    CURRENT GREEN CHEMISTRY, 2015, 2 (03) : 319 - 338
  • [7] Palladium-Catalyzed Monoarylation of Aryl Amine with Aryl Tosylates
    Xie, Xiaomin
    Ni, Gang
    Ma, Fangfang
    Ding, Lina
    Xu, Sheng
    Zhang, Zhaoguo
    SYNLETT, 2011, (07) : 955 - 958
  • [8] Microwave-promoted aminocarbonylation of aryl iodides, aryl bromides, and aryl chlorides in water
    Wu, XY
    Ekegren, JK
    Larhed, M
    ORGANOMETALLICS, 2006, 25 (06) : 1434 - 1439
  • [9] Palladium-Catalyzed Aminocarbonylation of Aryl Halides
    Afsina, Cheriya Mukkolakkal Abdulla
    Philip, Rose Mary
    Saranya, Padinjare Veetil
    Anilkumar, Gopinathan
    CURRENT ORGANIC SYNTHESIS, 2023, 20 (03) : 308 - 331
  • [10] Trisodium heptaphosphide in reactions with alkyl and aryl tosylates
    Milyukov, V. A.
    Kataev, A. V.
    Hey-Hawkins, E.
    Sinyashin, O. G.
    RUSSIAN CHEMICAL BULLETIN, 2007, 56 (02) : 298 - 303