Copper-catalysed approach to spirocyclic oxindoles via a direct C-H, Ar-H functionalisation

被引:49
|
作者
Moody, Catherine L. [1 ]
Franckevicius, Vilius [1 ]
Drouhin, Pauline [1 ]
Klein, Johannes E. M. N. [1 ]
Taylor, Richard J. K. [1 ]
机构
[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England
关键词
Copper catalysis; Spirocyclic oxindoles; Radical cyclisation; C-H activation; Natural product synthesis; ANION CAPTURE PROCESSES; ENANTIOSELECTIVE SYNTHESIS; SUBSTITUTED OXINDOLES; ALPHA-ARYLATION; PALLADIUM; SPIROOXINDOLES; GELSEMINE; CENTERS; AMIDES; DERIVATIVES;
D O I
10.1016/j.tetlet.2012.01.120
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A practical and efficient entry to spirocyclic oxindoles from readily accessible anilide precursors, using only catalytic amounts of an inexpensive copper salt together with air as the sole re-oxidant, is described. In addition to providing access to a broad range of spiro-oxindole products, the utility of this method is demonstrated in a formal synthesis of the natural product, horsfiline. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1897 / 1899
页数:3
相关论文
共 50 条
  • [1] Copper-Mediated Construction of Spirocyclic Bis-oxindoles via a Double C-H, Ar-H Coupling Process
    Drouhin, Pauline
    Hurst, Timothy E.
    Whitwood, Adrian C.
    Taylor, Richard J. K.
    ORGANIC LETTERS, 2014, 16 (18) : 4900 - 4903
  • [2] Preparation of 3-Alkyl-Oxindoles by Copper(II)-Mediated C-H, Ar-H Coupling Followed by Decarboxyalkylation
    Pugh, David S.
    Klein, Johannes E. M. N.
    Perry, Alexis
    Taylor, Richard J. K.
    SYNLETT, 2010, (06) : 934 - 938
  • [3] Direct arylation of Thiophenes via palladium-catalysed C-H functionalisation at low catalyst loadings
    Battace, Ahmed
    Lemhadri, Mhamed
    Zair, Touriya
    Doucet, Henri
    Santelli, Maurice
    ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (16) : 2507 - 2516
  • [4] Benzylic ethers as arylcarboxy surrogates in substrate directed ortho C-H functionalisation catalysed by copper
    Khatun, Nilufa
    Banerjee, Arghya
    Santra, Sourav Kumar
    Ali, Wajid
    Patel, Bhisma K.
    RSC ADVANCES, 2015, 5 (46) : 36461 - 36466
  • [5] Iron-catalysed C-3 functionalisation of indolizines via C-H bond cleavage
    Xu Shao-hong
    JOURNAL OF CHEMICAL RESEARCH, 2012, (08) : 441 - 443
  • [6] Pd-catalysed C-H functionalisation of free carboxylic acids
    Dutta, Suparna
    Bhattacharya, Trisha
    Geffers, Finn J.
    Buerger, Marcel
    Maiti, Debabrata
    Werz, Daniel B.
    CHEMICAL SCIENCE, 2022, 13 (09) : 2551 - 2573
  • [7] Catalyst, additive and counterion effects on the efficiency and enantioselectivity of copper-catalysed C-H insertion reactions of α-diazosulfones
    Slattery, Catherine N.
    Clarke, Leslie-Ann
    Ford, Alan
    Maguire, Anita R.
    TETRAHEDRON, 2013, 69 (04) : 1297 - 1301
  • [8] Direct C-H borylation of vinylporphyrins via copper catalysis
    Belyaev, Evgeny S.
    Kozhemyakin, Grigory L.
    Tyurin, Vladimir S.
    Frolova, Victoria V.
    Lonin, Ivan S.
    Ponomarev, Gelii, V
    Buryak, Aleksey K.
    Zamilatskov, Ilya A.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (09) : 1926 - 1932
  • [9] Combined Experimental and Computational Investigations of Rhodium-Catalysed C-H Functionalisation of Pyrazoles with Alkenes
    Algarra, Andres G.
    Davies, David L.
    Khamker, Qudsia
    Macgregor, Stuart A.
    McMullin, Claire L.
    Singh, Kuldip
    Villa-Marcos, Barbara
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (07) : 3087 - 3096
  • [10] Substrate and Catalyst Effects in the Enantioselective Copper-Catalysed C-H Insertion Reactions of α-Diazo-β-oxo Sulfones
    Shiely, Amy E.
    Clarke, Leslie-Ann
    Flynn, Christopher J.
    Buckley, Aoife M.
    Ford, Alan
    Lawrence, Simon E.
    Maguire, Anita R.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (19) : 2277 - 2289