Synthesis of Novel Aryl and Heteroaryl Acyl Sulfonimidamides via Pd-Catalyzed Carbonylation Using a Nongaseous Precursor

被引:45
|
作者
Borhade, Sanjay R. [1 ]
Sandstrom, Anja [1 ]
Arvidsson, Per I. [1 ]
机构
[1] Uppsala Univ, Dept Med Chem BMC, SE-75123 Uppsala, Sweden
关键词
PROTEASE INHIBITORS; EX-SITU; BIOISOSTERES; SULFONAMIDES; ARYLATION;
D O I
10.1021/ol400049m
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Hitherto unexplored aryl and heteroaryl acyl sulfonimidamides have been prepared through the development of a new Pd-catalyzed carbonylation protocol. This novel methodology, employing sulfonimidamides as nucleophiles and CO gas ex situ released from solid Mo(CO)(6) in a sealed two-chamber system, yields a wide range of carbamate protected acyl sulfonimidamides in good to excellent yields.
引用
收藏
页码:1056 / 1059
页数:4
相关论文
共 50 条
  • [31] Biaryl synthesis via Pd-catalyzed decarboxylative coupling of aromatic carboxylates with aryl halides
    Goossen, Lukas J.
    Rodríguez, Nuria
    Melzer, Bettina
    Linder, Christophe
    Deng, Guojun
    Levy, Laura M.
    Journal of the American Chemical Society, 2007, 129 (15): : 4824 - 4833
  • [32] Biaryl synthesis via Pd-catalyzed decarboxylative coupling of aromatic carboxylates with aryl halides
    Goossen, Lukas J.
    Rodriguez, Nuria
    Melzer, Bettina
    Linder, Christophe
    Deng, Guojun
    Levy, Laura M.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (15) : 4824 - 4833
  • [33] Controlling Catalyst Speciation to Achieve Room Temperature Pd-Catalyzed Aminations with Aryl and Heteroaryl Chlorides
    Moreno, Mariur Rodriguez
    Setelin, Mary L.
    Hansen, Joshua D.
    Corey, James L.
    Noble, Kirt L.
    Stillwell, Lillian R.
    Angell, Emily
    Stubbs, Olivia A.
    Kumawat, Jugal
    Gomez, Carlos S. Munoz
    Smith, Stacey J.
    Ess, Daniel H.
    Michaelis, David J.
    ADVANCED SYNTHESIS & CATALYSIS, 2025,
  • [34] Mechanistic insight into the synergistic Cu/Pd-catalyzed carbonylation of aryl iodides using alcohols and dioxygen as the carbonyl source
    Junxuan Li
    Jinlei Zhou
    Yumei Wang
    Yue Yu
    Qiang Liu
    Tilong Yang
    Huoji Chen
    Hua Cao
    Science China(Chemistry) , 2022, (01) : 68 - 74
  • [35] Mechanistic insight into the synergistic Cu/Pd-catalyzed carbonylation of aryl iodides using alcohols and dioxygen as the carbonyl source
    Li, Junxuan
    Zhou, Jinlei
    Wang, Yumei
    Yu, Yue
    Liu, Qiang
    Yang, Tilong
    Chen, Huoji
    Cao, Hua
    SCIENCE CHINA-CHEMISTRY, 2022, 65 (01) : 68 - 74
  • [36] Mechanistic insight into the synergistic Cu/Pd-catalyzed carbonylation of aryl iodides using alcohols and dioxygen as the carbonyl source
    Junxuan Li
    Jinlei Zhou
    Yumei Wang
    Yue Yu
    Qiang Liu
    Tilong Yang
    Huoji Chen
    Hua Cao
    Science China(Chemistry), 2022, 65 (01) : 68 - 74
  • [37] Mechanistic insight into the synergistic Cu/Pd-catalyzed carbonylation of aryl iodides using alcohols and dioxygen as the carbonyl source
    Junxuan Li
    Jinlei Zhou
    Yumei Wang
    Yue Yu
    Qiang Liu
    Tilong Yang
    Huoji Chen
    Hua Cao
    Science China Chemistry, 2022, 65 : 68 - 74
  • [38] Late-stage Pd-catalyzed Cyanations of Aryl/Heteroaryl Halides in Aqueous Micellar Media
    Thakore, Ruchita R.
    Takale, Balaram S.
    Singhania, Vani
    Gallou, Fabrice
    Lipshutz, Bruce H.
    CHEMCATCHEM, 2021, 13 (01) : 212 - 216
  • [39] Synthesis of 3-Indazolecarboxylic Esters and Amides via Pd-Catalyzed Carbonylation of 3-Iodoindazoles
    Buchstaller, Hans-Peter
    Wilkinson, Kai
    Burek, Kasimir
    Nisar, Yasmin
    SYNTHESIS-STUTTGART, 2011, (19): : 3089 - 3098
  • [40] Scalable and Chemoselective Synthesis of γ-Keto Esters and Acids via Pd-Catalyzed Carbonylation of Cyclic β-Chloro Enones
    Kaplan, Justin M.
    Hruszkewycz, Damian P.
    Strambeanu, Iulia I.
    Nunn, Christopher J.
    VanGelder, Kelsey F.
    Dunn, Anna L.
    Wozniak, Derek I.
    Dobereiner, Graham E.
    Leitch, David C.
    ORGANOMETALLICS, 2019, 38 (01) : 85 - 96