Peng Wang, Xia Chen, Dong-Liang Wang, Yong-Qi Li, Ye Liu. Efficient and recyclable Rh-catalytic system with involvement of phosphine-functionalized phosphonium-based ionic liquids for tandem hydroformylation–acetalization. Green Energy&Environment, 2017, 2(4): 419-427. doi: 10.1016/j.gee.2017.01.003
Citation: Peng Wang, Xia Chen, Dong-Liang Wang, Yong-Qi Li, Ye Liu. Efficient and recyclable Rh-catalytic system with involvement of phosphine-functionalized phosphonium-based ionic liquids for tandem hydroformylation–acetalization. Green Energy&Environment, 2017, 2(4): 419-427. doi: 10.1016/j.gee.2017.01.003

Efficient and recyclable Rh-catalytic system with involvement of phosphine-functionalized phosphonium-based ionic liquids for tandem hydroformylation–acetalization

doi: 10.1016/j.gee.2017.01.003
  • The phosphine-functionalized phosphonium-based ionic liquids ( dppm-Q , dppe-Q , dppp-Q and dppb-Q ) as the bi-functional ligands enable the efficient one-pot tandem hydroformylation–acetalization. It was found that, in dppm-Q , dppe-Q , dppp-Q and dppb-Q , the incorporated phosphino-fragments were responsible for Rh-catalyzed hydroformylation and the phosphoniums were in charge of the subsequent acetalization as the Lewis acid catalysts. Moreover, the diphosphonium-based ionic liquid of dppb-DQ could be applied as a co-solvent to immobilize the Rh/ dppb-Q catalytic system with the advantages of the improved catalytic performance, the available catalyst recyclability, and the wide generality for the substrates.

     

  • loading
  • [1]
    H.D.Gesser, N.R.Hunter Catal. Today, 42 (1998),pp. 183-189
    [2]
    R.Franke, D.Selent, A.Börner Chem. Rev., 112 (2012),pp. 5675-5732
    [3]
    S.Chercheja, T.Rothenbucher, P.Eilbracht Adv. Synth. Catal., 351 (2009),pp. 339-344
    [4]
    X.Fang, R.Jackstell, R.Franke, et al. Chem. Eur. J., 20 (2014),pp. 13210-13216
    [5]
    X.Fang, R.Jackstell, M.Beller Chem. Eur. J., 20 (2014),pp. 7939-7942
    [6]
    X.Fang, H.Li, RalfJackstell, et al. J. Am. Chem. Soc., 136 (2014),pp. 16039-16043
    [7]
    X.Jin, K.Zhao, F.F.Cui, et al. Green Chem., 15 (2013),pp. 3236-3242
    [8]
    J.Balue, J.C.Bayon J. Mol. Catal. A Chem., 137 (1999),pp. 193-203
    [9]
    G.Parrinello, J.K.Stille J. Am. Chem. Soc., 109 (1987),pp. 7122-7127
    [10]
    M.C.de Freitas, C.G.Vieira, E.N.dos Santos, et al. ChemCatChem., 5 (2013),pp. 1884-1890
    [11]
    Q.Zhao, S.Li, K.Huang, et al. Org. Lett., 15 (2013),pp. 4014-4017
    [12]
    A.W.S.Currie, J.A.M.Andersen Catal. Lett., 44 (1997),pp. 106-110
    [13]
    Z.Xu, L.Liu, K.Wheeler, et al. Angew. Chem. Int. Ed., 50 (2011),pp. 3484-3488
    [14]
    T.Smejkal, D.Gribkov, J.Geier, et al. Chem. Eur. J., 16 (2010),pp. 2470-2478
    [15]
    D.Fuchs, G.Rousseau, L.Diab, et al. Angew. Chem. Int. Ed., 51 (2012),pp. 2178-2182
    [16]
    R.P.J.Bronger, S.M.Silva, P.C.J.Kamer, et al. Chem. Commun. (2002),pp. 3044-3045
    [17]
    X.F.Wu, X.Fang, L.Wu, et al. Acc. Chem. Res., 47 (2014),pp. 1041-1053
    [18]
    E.Boymans, M.Janssen, C.Müller, et al. Dalton Trans., 42 (2013),pp. 137-142
    [19]
    P.Eilbracht, L.Bärfacker, C.Buss, et al. Chem. Rev., 99 (1999),pp. 3329-3366
    [20]
    Y.Jin, J.Shi, F.Zhang, et al. J. Mol. Catal. A Chem., 383 (2014),pp. 167-171
    [21]
    M.M.Diwakar, R.M.Deshpande, R.V.Chaudhari J. Mol. Catal. A Chem., 232 (2005),pp. 179-186
    [22]
    J.Noronder, C.Rodrigues, A.Borner J. Mol. Catal. A Chem., 391 (2014),pp. 139-143
    [23]
    S.R.Khan, B.M.Bhanage Tetrahedron Lett., 54 (2013),pp. 5998-6001
    [24]
    A.E.Allen, D.W.C.MacMillan Chem. Sci., 3 (2012),pp. 633-658
    [25]
    P.Daka, Z.Xu, A.Alexa, et al. Chem. Commun., 47 (2011),pp. 224-226
    [26]
    F.Lv, S.Liu, W.Hu Asian J. Org. Chem., 2 (2013),pp. 824-836
    [27]
    R.Malacea, F.Chahdoura, M.Devillard, et al. Adv. Synth. Catal., 355 (2013),pp. 2274-2284
    [28]
    C.L.Joe, K.L.Tan J. Org. Chem., 76 (2011),pp. 7590-7596
    [29]
    Y.Q.Li, P.Wang, H.Liu, et al. Green Chem., 18 (2016),pp. 1798-1806
    [30]
    P.Wang, H.Liu, Y.Q.Li, et al. Catal. Sci. Technol., 6 (2016),pp. 3854-3861
    [31]
    T.W.Hudnall, Y.M.Kim, M.W.P.Bebbington, et al. J. Am. Chem. Soc., 130 (2008),pp. 10890-10891
    [32]
    C.B.Caputo, L.J.Hounjet, R.Dobrovetsky, et al. Science, 341 (2013),pp. 1374-1382
    [33]
    T.Mukaiyama, S.Matsui, K.Kashiwagi Chem. Lett. (1989),pp. 993-996
    [34]
    C.Tan, P.Wang, H.Liu, et al. Chem. Commun., 51 (2015),pp. 10871-10874
    [35]
    Y.Q.Li, H.Liu, P.Wang, et al. Faraday Discuss., 190 (2016),pp. 219-230
    [36]
    S.J.Chen, Y.Y.Wang, W.M.Yao, et al. J. Mol. Catal. A Chem., 378 (2013),pp. 293-298
    [37]
    T.E.Kunene, P.B.Webb, D.J.C.Hamilton Green Chem., 13 (2011),pp. 1476-1481
    [38]
    C.Kolbeck, N.Paape, T.Cremer, et al. Chem. Eur. J., 16 (2010),pp. 12083-12087
    [39]
    Y.Yuan, N.Yan, P.J.Dyson ACS Catal., 2 (2012),pp. 1057-1069
    [40]
    S.Sviatlana, Z.F.Fei, N.Yan, et al. Chimia, 69 (2015),pp. 592-596
    [41]
    W.Allen, B.F.Taylor Dalton Trans., 1 (1982),p. 51
    [42]
    S.Rrez, M.A.M.Rojas, A.Pizzano Organometallics, 21 (2002),pp. 4611-4621
    [43]
    M.S.Hill, P.B.Hitchcock J. Chem. Soc. Dolton Trans., 0 (2002),pp. 4694-4702
    [44]
    DieterFenske, ClaudiaPersau, StefanieDehnen, et al. Angew. Chem. Int. Ed., 43 (2004),pp. 305-309
  • 加载中

Catalog

    通讯作者: 陈斌, bchen63@163.com
    • 1. 

      沈阳化工大学材料科学与工程学院 沈阳 110142

    1. 本站搜索
    2. 百度学术搜索
    3. 万方数据库搜索
    4. CNKI搜索

    Article Metrics

    Article views (131) PDF downloads(10) Cited by()
    Proportional views

    /

    DownLoad:  Full-Size Img  PowerPoint
    Return
    Return