Practical and General Manganese-Catalyzed Carbonylative Coupling of Alkyl Iodides with Amides

被引:34
作者
Li, Yahui [1 ]
Zhu, Fengxiang [1 ]
Wang, Zechao [1 ]
Rabeah, Jabor [1 ]
Brueckner, Angelika [1 ]
Wu, Xiao-Feng [2 ]
机构
[1] Univ Rostock, Leibniz Inst Katalyse eV, Albert Einstein Str 29a, D-18059 Rostock, Germany
[2] Zhejiang Sci Tech Univ, Dept Chem, Xiasha Campus, Hangzhou 310018, Zhejiang, Peoples R China
关键词
alkyl halides; amides; carbonylation; imides; manganese; METAL-METAL BONDS; PINCER COMPLEXES; CARBON-MONOXIDE; IMIDES; NUCLEOPHILES; EFFICIENT; NITRILES; RADICALS; STRATEGY; ALKENES;
D O I
10.1002/cctc.201601712
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
A selective manganese-catalyzed carbonylative transformation of alkyl iodides and amides was developed. A variety of imides were prepared in moderate to good yields. Alkyl bromides could also be applied by in situ treatment with NaI to give the corresponding alkyl iodides. Notably, no additives or expensive ligands were required here. As the first example of the carbonylative coupling of alkyl iodides with amides, the simple reaction conditions and the advantages of a manganese catalyst make this new general procedure more attractive and practical than conventional techniques. Mechanistically, control experiments and electron paramagnetic resonance spectroscopy studies were also performed, and the radical nature of this new process was proven.
引用
收藏
页码:915 / 919
页数:5
相关论文
共 56 条
  • [1] Synthesis and X-ray crystallographic structure of leucine-phenylalanyl succinimide-based pseudopeptides
    Abell, AD
    Oldham, MD
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (05) : 1509 - 1513
  • [2] GAS-PHASE PYROLYTIC REACTIONS .5. RATE DATA FOR PYROLYSIS OF N-TERT-BUTYL-BENZAMIDE AND N-ACETYL-BENZAMIDE, N-ACETYL-N-METHYLACETAMIDE, AND N-ETHYL-2-YL-THIOACETAMIDE AND N-PROP-2-YL-THIOACETAMIDE
    ALAWADI, NA
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1990, (12): : 2187 - 2189
  • [3] [Anonymous], 1999, MERCK IND VERS 12 3
  • [4] [Anonymous], 2015, ANGEW CHEM INT EDIT
  • [5] Methyllycaconitine analogues have mixed antagonist effects at nicotinic acetylcholine receptors
    Barker, D
    Lin, DHS
    Carland, JE
    Chu, CPY
    Chebib, M
    Brimble, MA
    Savage, GP
    McLeod, MD
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (14) : 4565 - 4575
  • [6] Palladium-Catalyzed Carbonylation-A Reaction Come of Age
    Barnard, Christopher F. J.
    [J]. ORGANOMETALLICS, 2008, 27 (21) : 5402 - 5422
  • [7] Recent Synthetic Applications of Manganese in Organic Synthesis
    Concellon, Jose M.
    Rodriguez-Solla, Humberto
    del Amo, Vicente
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (33) : 10184 - 10191
  • [8] Synthesis of a malimide analogue of the telomerase inhibitor UCS1025A using a dianionic aldol strategy
    de Figueiredo, Renata Marcia
    Voith, Matthias
    Froehlich, Roland
    Christmann, Mathias
    [J]. SYNLETT, 2007, (03) : 391 - 394
  • [9] Efficient and selective N-alkylation of amines with alcohols catalysed by manganese pincer complexes
    Elangovan, Saravanakumar
    Neumann, Jacob
    Sortais, Jean-Baptiste
    Junge, Kathrin
    Darcel, Christophe
    Beller, Matthias
    [J]. NATURE COMMUNICATIONS, 2016, 7
  • [10] Selective Catalytic Hydrogenations of Nitriles, Ketones, and Aldehydes by Well-Defined Manganese Pincer Complexes
    Elangovan, Saravanakumar
    Topf, Christoph
    Fischer, Steffen
    Jiao, Haijun
    Spannenberg, Anke
    Baumann, Wolfgang
    Ludwig, Ralf
    Junge, Kathrin
    Beller, Matthias
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (28) : 8809 - 8814