Palladium-Catalyzed Reductive Carbonylation of Aryl Halides with N-Formylsaccharin as a CO Source

被引：196
作者：
Ueda, Tsuyoshi [1 ,2 ]
Konishi, Hideyuki [1 ]
Manabe, Kei [1 ]
机构：
[1] Univ Shizuoka, Sch Pharmaceut Sci, Suruga Ku, Shizuoka 4228526, Japan
[2] Daiichi Sankyo Co Ltd, Pharmaceut Technol Div, Proc Technol Res Labs, Hiratsuka, Kanagawa 2540014, Japan
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 33期
关键词：
aldehydes; arenes; carbonylation; palladium; synthetic methods; ATMOSPHERIC-PRESSURE; VINYL HALIDES; EFFICIENT; BROMIDES; FORMATE; HYDROXYCARBONYLATION; FORMYLATION; ALKOXYCARBONYLATION; DECARBONYLATION; CHLORIDES;
D O I：
10.1002/anie.201303926
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Easy peasy: The title reaction employs N-formylsaccharin, which is an easily accessible crystalline compound, as an effective CO source. The reactions proceed with a small excess of the CO source at moderate temperatures and were successfully applied to a wide range of aryl bromides. DMF=N,N- dimethylformamide, dppb=1,4-bis-(diphenylphosphino)butane. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：8611 / 8615
页数：5
相关论文
共 38 条
  • [1] Reductive carbonylation - an efficient and practical catalytic route for the conversion of aryl halides to aldehydes
    Ashfield, Laura
    Barnard, Christopher F. J.
    [J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2007, 11 (01) : 39 - 43
  • [2] Palladium-catalyzed hydroxycarbonylation of aryl and vinyl bromides by mixed acetic formic anhydride
    Berger, Philippe
    Bessmernykh, Alla
    Caille, Jean-Claude
    Mignonac, Sylviane
    [J]. SYNTHESIS-STUTTGART, 2006, (18): : 3106 - 3110
  • [3] Palladium-Catalyzed Carbonylation Reactions of Aryl Halides and Related Compounds
    Brennfuehrer, Anne
    Neumann, Helfried
    Beller, Matthias
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (23) : 4114 - 4133
  • [4] Brennfuhrer A., 2009, ANGEW CHEM, V121, P4176
  • [5] Palladium-catalyzed synthesis of aldehydes from aryl iodides and acetic formic anhydride
    Cacchi, S
    Fabrizi, G
    Goggiamani, A
    [J]. JOURNAL OF COMBINATORIAL CHEMISTRY, 2004, 6 (05): : 692 - 694
  • [6] Palladium-catalyzed hydroxycarbonylation of aryl and vinyl halides or triflates by acetic anhydride and formate anions
    Cacchi, S
    Fabrizi, G
    Goggiamani, A
    [J]. ORGANIC LETTERS, 2003, 5 (23) : 4269 - 4272
  • [7] A NOVEL AND CONVENIENT METHOD FOR PALLADIUM-CATALYZED ALKOXYCARBONYLATION OF ARYL AND VINYL HALIDES USING HCO2R/NAOR SYSTEM
    CARPENTIER, JF
    CASTANET, Y
    BROCARD, J
    MORTREUX, A
    PETIT, F
    [J]. TETRAHEDRON LETTERS, 1991, 32 (36) : 4705 - 4708
  • [8] N-Formylsaccharin: A New Formylating Agent
    Cochet, Thomas
    Bellosta, Veronique
    Greiner, Alfred
    Roche, Didier
    Cossy, Janine
    [J]. SYNLETT, 2011, (13) : 1920 - 1922
  • [9] Silacarboxylic Acids as Efficient Carbon Monoxide Releasing Molecules: Synthesis and Application in Palladium-Catalyzed Carbonylation Reactions
    Friis, Stig D.
    Taaning, Rolf H.
    Lindhardt, Anders T.
    Skrydstrup, Troels
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (45) : 18114 - 18117
  • [10] Palladium-catalyzed esterification of aryl halides using aryl formates without the use of external carbon monoxide
    Fujihara, Tetsuaki
    Hosoki, Tomoya
    Katafuchi, Yuko
    Iwai, Tomohiro
    Terao, Jun
    Tsuji, Yasushi
    [J]. CHEMICAL COMMUNICATIONS, 2012, 48 (64) : 8012 - 8014
1234