Oxalic acid as the in situ carbon monoxide generator in palladium-catalyzed hydroxycarbonylation of arylhalides

被引:36
|
作者
Shao, Changdong [1 ,2 ]
Lu, Ailan [1 ]
Wang, Xiaoling [1 ]
Zhou, Bo [1 ]
Guan, Xiaohong [2 ,3 ]
Zhang, Yanghui [1 ,2 ,4 ]
机构
[1] Tongji Univ, Sch Chem Sci & Engn, 1239 Siping Rd, Shanghai 200092, Peoples R China
[2] Tongji Univ, UNEP Tongji Inst Environm Sustainable Dev, 1239 Siping Rd, Shanghai 200092, Peoples R China
[3] Tongji Univ, Coll Environm Sci & Engn, 1239 Siping Rd, Shanghai 200092, Peoples R China
[4] Shanghai Key Lab Chem Assessment & Sustainabil, 1239 Siping Rd, Shanghai 200092, Peoples R China
基金
中国国家自然科学基金;
关键词
KHAND-TYPE REACTION; LARGE-SCALE APPLICATIONS; ARYL HALIDES; EX-SITU; CARBONYLATION REACTIONS; COUPLING REACTIONS; N-FORMYLSACCHARIN; ORGANIC HALIDES; CO; CARBOXYLATION;
D O I
10.1039/c7ob01052d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient palladium-catalyzed hydroxycarbonylation reaction of arylhalides using oxalic acid as a CO source has been developed. The reaction features high safety, low catalyst loading, and a broad substrate scope, and provides a safe and tractable approach to access a variety of aromatic carboxylic acid compounds. Mechanistic studies revealed the decomposition pattern of oxalic acid.
引用
收藏
页码:5033 / 5040
页数:8
相关论文
共 50 条
  • [41] PALLADIUM-CATALYZED CARBONYLATIVE VINYLATION OF ARYLMERCURIC CHLORIDES WITH CARBON-MONOXIDE AND OLEFINS
    RYU, DS
    SONG, KH
    LEE, JT
    KIM, JI
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 1992, 13 (04) : 354 - 355
  • [42] Palladium-Catalyzed Ring-Opening Thiocarbonylation of Vinylcyclopropanes with Thiols and Carbon Monoxide
    Li, Chang-Feng
    Xiao, Wen-Jin
    Alper, Howard
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (02): : 888 - 890
  • [43] Highly stereoselective palladium-catalyzed dithiocarbonylation of propargylic mesylates with thiols and carbon monoxide
    Xiao, WJ
    Alper, H
    JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (05): : 1802 - 1807
  • [44] Synthesis of Indoles by Palladium-Catalyzed Reductive Cyclization of -Nitrostyrenes with Carbon Monoxide as the Reductant
    Ferretti, Francesco
    El-Atawy, Mohamed A.
    Muto, Stefania
    Hagar, Mohamed
    Gallo, Emma
    Ragaini, Fabio
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (26) : 5712 - 5715
  • [46] Palladium-catalyzed enantioselective carbonylative cyclization of aryl and alkenyl triflates with carbon monoxide
    Hayashi, T
    Tang, J
    Kato, K
    ORGANIC LETTERS, 1999, 1 (09) : 1487 - 1489
  • [47] Palladium-catalyzed carbonylative lactonization of propargyl alcohols with organic dichalcogenides and carbon monoxide
    Ogawa, A
    Kuniyasu, H
    Sonoda, N
    Hirao, T
    JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (24): : 8361 - 8365
  • [49] Ligand electronic effect in enantioselective palladium-catalyzed copolymerization of carbon monoxide and propene
    Gambs, Celine
    Chaloupka, Stanislav
    Consiglio, Giambattista
    Togni, Antonio
    Angewandte Chemie (International Edition in English), 2000, 39 (14): : 2486 - 2488
  • [50] Mechanistic Studies of Palladium-Catalyzed Aminocarbonylation of Aryl Chlorides with Carbon Monoxide and Ammonia
    Wang, Justin Y.
    Strom, Alexandra E.
    Hartwig, John F.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (25) : 7979 - 7993