Volume 8 Issue 4
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Wenfeng Zhao, Hu Li, Heng Zhang, Song Yang, Anders Riisager. Ammonia borane-enabled hydrogen transfer processes: Insights into catalytic strategies and mechanisms. Green Energy&Environment, 2023, 8(4): 948-971. doi: 10.1016/j.gee.2022.03.011
Citation: Wenfeng Zhao, Hu Li, Heng Zhang, Song Yang, Anders Riisager. Ammonia borane-enabled hydrogen transfer processes: Insights into catalytic strategies and mechanisms. Green Energy&Environment, 2023, 8(4): 948-971. doi: 10.1016/j.gee.2022.03.011
shu

Ammonia borane-enabled hydrogen transfer processes: Insights into catalytic strategies and mechanisms

doi: 10.1016/j.gee.2022.03.011

  • a. State Key Laboratory Breeding Base of Green Pesticide & Agricultural Bioengineering, Key Laboratory of Green Pesticide & Agricultural Bioengineering, Ministry of Education, State-Local Joint Laboratory for Comprehensive Utilization of Biomass, Center for Research & Development of Fine Chemicals, Guizhou University, Guiyang, 550025, China;

  • b. Centre for Catalysis and Sustainable Chemistry, Department of Chemistry, Kemitorvet Building 207, Technical University of Denmark, DK-2800 Kgs. Lyngby, Denmark

Funds:

This study was financially supported by the National Natural Science Foundation of China (21908033, 21576059, 21666008), Fok Ying-Tong Education Foundation (161030), the Program of Introducing Talents of Discipline to Universities of China (111 Program, D20023), and Guizhou Frontiers Science Center for Asymmetric Synthesis and Medicinal Molecules ([2020]004).

  • Received date 14 January 2022, Accepted date 28 March 2022, RevRecd date 25 March 2022, Publish date 05 April 2022,
    Abstract
  • Transfer hydrogenation (TH) with in situ generated hydrogen donor is of great importance in reduction reactions, and an alternative strategy to traditional hydrogenation processes involving pressurized molecular hydrogen. Ammonia borane (NH3BH3, AB) is a promising material of hydrogen storage, and it has attracted much attention in reductive organic transformations owing to its high activity, good atom economy, non-toxicity, sustainability, and ease of transport and storage. This review focuses on summarizing the recent progress of AB-mediated TH reactions of diverse substrates including nitro compounds, nitriles, imines, alkenes, alkynes, carbonyl compounds (ketones and aldehydes), carbon dioxide, and N- and O-heterocycles. Syntheses protocols (metal-containing and metal-free), the effect of reaction parameters, product distribution, and variation of reactivity are surveyed, and the mechanism of each reaction involving the action mode of AB as well as structure-activity relationships is discussed in detail. Finally, perspectives are presented to highlight the challenges and opportunities for AB-enabled TH reactions of unsaturated compounds.

     

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  • [1]
    S. Anis, Z.A. Zainal, Renew. Sust. Energ. Rev. 15 (2011) 2355-2377.
    [2]
    G. Brieger, T.J. Nestrick, Chem. Rev. 74 (1974) 567-580.
    [3]
    P. Janulis, Renew. Energ. 29 (2004) 861-871.
    [4]
    P. Etayo, A. Vidal-Ferran, Chem. Soc. Rev. 42 (2013) 728-754.
    [5]
    N.B. Johnson, I.C. Lennon, P.H. Moran, J.A. Ramsden, Accounts Chem. Res. 40 (2007) 1291-1299.
    [6]
    D.H. Lloyd, D.E. Nichols, J. Org. Chem. 51 (1986) 4294-4295
    [7]
    M.L.V. Rios, A.M. Gonzalez, E.E.S. Lora, O.a.A. Del Olmo, Biomass Bioenerg. 108 (2018) 345-370.
    [8]
    H.U. Blaser, C. Malan, B. Pugin, F. Spindler, H. Steiner, M. Studer, Adv. Synth. Catal. 345 (2003) 103-151.
    [9]
    D.-S. Wang, Q.-A. Chen, S.-M. Lu, Y.-G. Zhou, Chem. Rev. 112 (2012) 2557-2590.
    [10]
    P.A. Dub, T. Ikariya, ACS Catal. 2 (2012) 1718-1741.
    [11]
    M.J. Gilkey, B. Xu, ACS Catal. 6 (2016) 1420-1436.
    [12]
    J. Song, Z.-F. Huang, L. Pan, K. Li, X. Zhang, L. Wang, J.-J. Zou, Appl. Catal. B-Environ. 227 (2018) 386-408.
    [13]
    H. Valdes, M.A. Garcia-Eleno, D. Canseco-Gonzalez, D. Morales-Morales, ChemCatChem 10 (2018) 3136-3172.
    [14]
    H. Yang, C. Zhang, P. Gao, H. Wang, X. Li, L. Zhong, W. Wei, Y. Sun, Catal. Sci. Technol. 7 (2017) 4580-4598.
    [15]
    I. Regla, A. Reyes, C. Korber, P. Demare, O. Estrada, E. Juaristi, Syn.Commun. 27 (1997) 817-823.
    [16]
    V.I. Anikeev, V.P. Sivcev, K.R. Valeev, K.P. Volcho, V.A. Sadykov, N.F. Salakhutdinov, J. Supercrit. Fluid. 140 (2018) 233-237.
    [17]
    S. Jaatinen, R. Karinen, Top. Catal. 60 (2017) 1473-1481.
    [18]
    R.Z.H. Wang, X. Y.; Xu, J.; Liu, P.; Li, F. , J. Org. Chem. 85 (2018) 2242-2249.
    [19]
    A.K. Singh, S. Singh, A. Kumar, Catal. Sci. Technol. 6 (2016) 12-40.
    [20]
    R. Nie, Y. Tao, Y. Nie, T. Lu, J. Wang, Y. Zhang, X. Lu, C.C. Xu, ACS Catal. 11 (2021) 1071-1095.
    [21]
    A.H. Romero, ChemistrySelect 5 (2020) 13054-13075.
    [22]
    D.A. Bulushev, J.R.H. Ross, Catal. Today 163 (2011) 42-46.
    [23]
    B.Y. Cao, S. Xu, Y.L. Ren, Y. Yu, J.Y. Guo, L. Zhang, N. Li, G.C. Zhang, C.S. Zhou, Chem. Lett. 46 (2017) 1773-1776.
    [24]
    K. Fulajtarova, M. Hronec, T. Liptaj, N.A. Pronayova, T. Sotak, J. Taiwan Inst. Chem. E. 66 (2016) 137-142.
    [25]
    W. Zhao, H. Li, Y. Li, J. Long, Y. Xu, S. Yang, Sustain. Chem. Pharm. 17 (2020).
    [26]
    W. Wu, W. Zhao, C. Fang, Z. Wang, T. Yang, H. Li, S. Yang, Catal. Commun. 105 (2018) 6-10.
    [27]
    A. Sanagawa, H. Nagashima, Org. Lett. 21 (2019) 287-291.
    [28]
    N. Sakai, K. Fujii, S. Nabeshima, R. Ikeda, T. Konakahara, Chem. Commun. 46 (2010) 3173-3175.
    [29]
    R.N. Naumov, M. Itazaki, M. Kamitani, H. Nakazawa, J. Am. Chem. Soc. 134 (2012) 804-807.
    [30]
    H. Li, W. Zhao, S. Saravanamurugan, W. Dai, J. He, S. Meier, S. Yang, A. Riisager, Commun. Chem. 1 (2018).
    [31]
    H. Li, W. Zhao, W. Dai, J. Long, M. Watanabe, S. Meier, S. Saravanamurugan, S. Yang, A. Riisager, Green Chem. 20 (2018) 5327-5335.
    [32]
    B. Fu, X. Yuan, Y. Li, Y. Wang, Q. Zhang, T. Xiong, Q. Zhang, Org. Lett. 21 (2019) 3576-3580.
    [33]
    X.-F. Bai, L.-W. Xu, L.-S. Zheng, J.-X. Jiang, G.-Q. Lai, J.-Y. Shang, Chem. Eur. J. 18 (2012) 8174-8179.
    [34]
    D.W. Himmelberger, L.R. Alden, M.E. Bluhm, L.G. Sneddon, Inorg. Chem. 48 (2009) 9883-9889.
    [35]
    F.H. Stephens, V. Pons, R. Tom Baker, Dalton Trans. (2007) 2613-2626.
    [36]
    M. Hasenbeck, J. Becker, U. Gellrich, Angew. Chem. Int. Ed. 59 (2020) 1590-1594.
    [37]
    B. Peng, J. Chen, Energ. Environ. Sci. 1 (2008) 479-483.
    [38]
    U.B. Demirci, Int. J. Hydrogen Energ. 42 (2017) 9978-10013.
    [39]
    C.-C. Chou, B.-H. Chen, J. Power Sources 293 (2015) 343-350.
    [40]
    M. Chandra, Q. Xu, J. Power Sources 159 (2006) 855-860.
    [41]
    C.-C. Chou, D.-J. Lee, B.-H. Chen, Int. J. Hydrogen Energ. 37 (2012) 15681-15690.
    [42]
    H. Dong, H. Berke, J. Organomet. Chem. 696 (2011) 1803-1808.
    [43]
    M. Hu, J. Van Paasschen, R. Geanangel, J. Inorg. Nucl. Chem. 39 (1977) 2147-2150.
    [44]
    M. Mostajeran, D.J. Wolstenholme, C. Frazee, G.S. Mcgrady, R.T. Baker, Chem. Commun. 52 (2016) 2581-2584.
    [45]
    X. Chen, X. Bao, B. Billet, S.G. Shore, J.-C. Zhao, Chem. Eur. J. 18 (2012) 11994-11999.
    [46]
    P.V. Ramachandran, H. Mistry, A.S. Kulkarni, P.D. Gagare, Dalton Trans. 43 (2014) 16580-16583.
    [47]
    E.R. Burkhardt, B.M. Coleridge, Tetrahedron Lett. 49 (2008) 5152-5155.
    [48]
    Y. Tan, L. Zhang, X. Chen, X. Yu, Dalton Trans. 44 (2015) 753-757.
    [49]
    S. Hausdorf, F. Baitalow, G. Wolf, F.O.R.L. Mertens, Int. J. Hydrogen Energ. 33 (2008) 608-614.
    [50]
    N.C. Smythe, J.C. Gordon, Eur.J. Inorg. Chem. 2010 (2010) 509-521.
    [51]
    O.T. Summerscales, J.C. Gordon, Dalton Trans. 42 (2013) 10075-10084.
    [52]
    P. Veeraraghavan Ramachandran, B.C. Raju, P.D. Gagare, Org. Lett. 14 (2012) 6119-6121.
    [53]
    A.D. Sutton, A.K. Burrell, D.A. Dixon, E.B. Garner Iii, J.C. Gordon, T. Nakagawa, K.C. Ott, J.P. Robinson, M. Vasiliu, Science 331 (2011) 1426-1429.
    [54]
    P.M. Zimmerman, Z. Zhang, C.B. Musgrave, J. Phys. Chem. Lett. 2 (2011) 276-281.
    [55]
    S.-F. Hou, J.-Y. Chen, M. Xue, M. Jia, X. Zhai, R.-Z. Liao, C.-H. Tung, W. Wang, ACS Catal. 10 (2019) 380-390.
    [56]
    X. Yang, L. Zhao, T. Fox, Z.X. Wang, H. Berke, Angew. Chem. Int. Ed. 49 (2010) 2058-2062.
    [57]
    A.-M. Alexander, J.S.J. Hargreaves, Chem. Soc. Rev. 39 (2010) 4388-4401.
    [58]
    A. Corma, P. Concepcion, P. Serna, Angew. Chem. Int. Ed. 46 (2007) 7266-7269
    [59]
    A. Goswami, R.G. Kadam, J. Tucek, Z. Sofer, D. Bousa, R.S. Varma, M.B. Gawande, R. Zboril, Chem. Eng. J. 382 (2020) 122469
    [60]
    P.S. Kumar, K.M.L. Rai, Chem. Pap. 66 (2012) 772-778
    [61]
    T. Schwob, R. Kempe, Angew. Chem. Int. Ed. 55 (2016) 15175-15179
    [62]
    R. Raja, V.B. Golovko, J.M. Thomas, A. Berenguer-Murcia, W. Zhou, S. Xie, B.F.G. Johnson, Chem. Commun. (2005) 2026-2028.
    [63]
    B. Qiao, A. Wang, X. Yang, L.F. Allard, Z. Jiang, Y. Cui, J. Liu, J. Li, T. Zhang, Nature Chem. 3 (2011) 634-641
    [64]
    X.-F. Yang, A. Wang, B. Qiao, J. Li, J. Liu, T. Zhang, Accounts Chem. Res. 46 (2013) 1740-1748.
    [65]
    Y. Liu, D. Yin, Q. Xin, M. Lv, B. Bian, L. Li, C. Xie, S. Yu, S. Liu, Solid State Sci. 101 (2020) 106100.
    [66]
    K. Sarkar, K. Das, A. Kundu, D. Adhikari, B. Maji, ACS Catal. 11 (2021) 2786-2794
    [67]
    V. Babel, B.L. Hiran, Catal. Lett. (2020) 1-5
    [68]
    S. Cheng, X. Meng, N. Shang, S. Gao, C. Feng, C. Wang, Z. Wang, New J. Chem. 42 (2018) 1771-1778.
    [69]
    Q.H. Cui, L. Jiang, C. Zhang, Y.S. Zhao, W. Hu, J. Yao, Adv. Mater. 24 (2012) 2332-2336.
    [70]
    Q. Song, W.D. Wang, X. Hu, Z. Dong, Nanoscale 11 (2019) 21513-21521.
    [71]
    Z. Zou, Y. Jiang, K. Song, Catal. Lett. 150 (2020) 1277-1286.
    [72]
    M. Shen, H. Liu, C. Yu, Z. Yin, M. Muzzio, J. Li, Z. Xi, Y. Yu, S. Sun, J. Am. Chem. Soc. 140 (2018) 16460-16463.
    [73]
    J. Du, J. Chen, H. Xia, Y. Zhao, F. Wang, H. Liu, W. Zhou, B. Wang, ChemCatChem 12 (2020) 2426-2430.
    [74]
    Z. Ma, H. Liu, M. Yue, Nano Res. 12 (2019) 3085-3088.
    [75]
    J. Du, J. Hou, B. Li, R. Qin, C. Xu, H. Liu, J. Alloy Compd. 815 (2019) 152372.
    [76]
    T.-J. Zhao, Y.-N. Zhang, K.-X. Wang, J. Su, X. Wei, X.-H. Li, RSC Adv. 5 (2015) 102736-102740.
    [77]
    O. Metin, A. Mendoza-Garcia, D. Dalmizrak, M.S. Gultekin, S. Sun, Catal. Sci. Technol. 6 (2016) 6137-6143.
    [78]
    H. Goksu, S.F. Ho, O. Metin, K. Korkmaz, A.M. Garcia, M.S. Gultekin, S. Sun, ACS Catal. 4 (2014) 1777-1782.
    [79]
    J. Shabir, C. Garkoti, P. Gupta, M. Sharma, S. Rani, M. Kumari, S. Mozumdar, Acs Omega 6 (2021) 1415-1425.
    [80]
    O. Metin, H. Can, K. Sendil, M.S. Gultekin, J. Colloid Interf. Sci. 498 (2017) 378-386.
    [81]
    H. Goksu, H. Can, K. Sendil, M.S. Gultekin, O. Metin, Appl. Catal. A-Gen. 488 (2014) 176-182.
    [82]
    S. Byun, Y. Song, B.M. Kim, ACS Appl. Mater. Inter. 8 (2016) 14637-14647.
    [83]
    M. Muzzio, H. Lin, K. Wei, X. Guo, C. Yu, T. Yom, Z. Xi, Z. Yin, S. Sun, ACS Sustain. Chem. Eng. 8 (2020) 2814-2821.
    [84]
    Y.-H. Zhou, Q. Yang, Y.-Z. Chen, H.-L. Jiang, Chem. Commun. 53 (2017) 12361-12364.
    [85]
    C. Yu, J. Fu, M. Muzzio, T. Shen, D. Su, J. Zhu, S. Sun, Chem. Mater. 29 (2017) 1413-1418.
    [86]
    Y.-H. Zhou, S. Wang, Y. Wan, J. Liang, Y. Chen, S. Luo, C. Yong, J. Alloy Compd. 728 (2017) 902-909.
    [87]
    S. Cheng, Y. Liu, Y. Zhao, X. Zhao, Z. Lang, H. Tan, T. Qiu, Y. Wang, Dalton Trans. 48 (2019) 17499-17506.
    [88]
    H. Miao, K. Ma, H. Zhu, K. Yin, Y. Zhang, Y. Cui, RSC Adv. 9 (2019) 14580-14585.
    [89]
    X. Ma, Y.-X. Zhou, H. Liu, Y. Li, H.-L. Jiang, Chem. Commun. 52 (2016) 7719-7722.
    [90]
    Wang, Zhenzhen, Zhang, Haoyang, Chen, Lili, Miao, Songsong, Wu, Shujie, J. Phys. Chem. C 122 (2018) 12975-12983.
    [91]
    T. Su, Y. Jiang, Y. Xu, X. Luo, X. Xie, Z. Qin, H. Ji, React. Kinet. Mech. Cat. 131 (2020) 805-818.
    [92]
    S. Nie, S. Yang, P. Zhang, Chem. Eng. Sci. 220 (2020) 115619.
    [93]
    Y. Qu, T. Chen, Chem. Eng. J. 382 (2020).
    [94]
    A. Pei, L. Ruan, H. Fu, J. Liu, L. Zeng, H. Zhang, J. Hua, L. Zhu, B.H. Chen, CrystEngComm 22 (2020) 5382-5388.
    [95]
    Q. Zhang, J. Bu, J. Wang, C. Sun, D. Zhao, G. Sheng, X. Xie, M. Sun, L. Yu, ACS Catal. 10 (2020) 10350-10363.
    [96]
    Y. Wang, R. Qin, Y. Wang, J. Ren, W. Zhou, L. Li, J. Ming, W. Zhang, G. Fu, N. Zheng, Angew. Chem. Int. Ed. 59 (2020) 12736-12740.
    [97]
    V. Babel, B.L. Hiran, Catal. Lett. 150 (2020) 1865-1869.
    [98]
    Y. Xu, J. Long, W. Zhao, H. Li, S. Yang, Front. Chem. 7 (2019) 590.
    [99]
    L. Yu, Q. Zhang, S.-S. Li, J. Huang, Y.-M. Liu, H.-Y. He, Y. Cao, ChemSusChem 8 (2015) 3029-3035.
    [100]
    I. Sorribes, G. Wienhoefer, C. Vicent, K. Junge, R. Llusar, M. Beller, Angew. Chem. Int. Ed. 51 (2012) 7794-7798.
    [101]
    L. Zhang, L. Zhang, S. Cheng, X. Zhou, N. Shang, S. Gao, C. Wang, Appl. Organomet. Chem. 34 (2020) e5684.
    [102]
    H.D. Burge, D.J. Collins, B.H. Davis, Ind. Eng. Chem. Prod. Res. Dev. 19 (1980) 389-391.
    [103]
    J. Wang, C. Du, Q. Wei, W. Shen, Energ. Fuel. 35 (2021) 4358-4366.
    [104]
    Collect. Czech. Chem. C. 46 (1981) 1947-1957.
    [105]
    S. Chakraborty, H. Berke, ACS Catal. 4 (2014) 2191-2194.
    [106]
    Y.-F. Zen, Z.-C. Fu, F. Liang, Y. Xu, D.-D. Yang, Z. Yang, X. Gan, Z.-S. Lin, Y. Chen, W.-F. Fu, Asian J. Org. Chem. 6 (2017) 1589-1593.
    [107]
    Z. Shao, S. Fu, M. Wei, S. Zhou, Q. Liu, Angew. Chem. Int. Ed. 55 (2016) 14653-14657.
    [108]
    D.M. Sharma, B. Punji, Adv. Synth. Catal. 361 (2019) 3930-3936.
    [109]
    S.-F. Hou, J.-Y. Chen, M. Xue, M. Jia, X. Zhai, R.-Z. Liao, C.-H. Tung, W. Wang, ACS Catal. 10 (2020) 380-390.
    [110]
    S. Li, G. Li, W. Meng, H. Du, J. Am. Chem. Soc. 138 (2016) 12956-12962.
    [111]
    Q. Zhou, W. Meng, J. Yang, H. Du, Angew. Chem. Int. Ed. 57 (2018) 12111-12115.
    [112]
    B.J. Gregori, M. Nowakowski, A. Schoch, S. Pollath, J. Zweck, M. Bauer, A. Jacobi Von Wangelin, ChemCatChem 12 (2020) 5359-5363.
    [113]
    S.A. Jagtap, T. Sasaki, B.M. Bhanage, J. Mole. Catal. A-Chem. 414 (2016) 78-86.
    [114]
    J.A. Delgado, O. Benkirane, C. Claver, D. Curulla-Ferre, C. Godard, Dalton Trans. 46 (2017) 12381-12403.
    [115]
    E. Kim, S. Kim, B.M. Kim, B. Korean Chem. Soc. 32 (2011) 3183-3186.
    [116]
    M.-K. Ji, D.-H. Yoon, H.-J. Ha, P. Kang, W.K. Lee, B. Korean Chem. Soc. 33 (2012) 2853-2854.
    [117]
    T.N. Gieshoff, M. Villa, A. Welther, M. Plois, U. Chakraborty, R. Wolf, A.J. von Wangelin, Green Chem. 17 1408-1413.
    [118]
    I.M. Baibich, R. Garcia, J. Brazil Chem. Soc. 8 (1997) 215-218.
    [119]
    A. Comas-Vives, G. Ujaque, J. Am. Chem. Soc. 135 (2013) 1295-1305.
    [120]
    E. Vasilikogiannaki, I. Titilas, G. Vassilikogiannakis, M. Stratakis, Chem. Commun. 51 (2015) 2384-2387.
    [121]
    H. Liang, B. Zhang, H. Ge, X. Gu, S. Zhang, Y. Qin, ACS Catal. 7 (2017) 6567-6572.
    [122]
    S. Rej, M. Madasu, C.-S. Tan, C.-F. Hsia, M.H. Huang, Chem. Sci. 9 (2018) 2517-2524.
    [123]
    V.R. Bakuru, B. Velaga, N.R. Peela, S.B. Kalidindi, Chem. Eur. J. 24 (2018) 15978-15982.
    [124]
    V.R. Bakuru, D. Samanta, T.K. Maji, S.B. Kalidindi, Dalton Trans. 49 (2020) 5024-5028.
    [125]
    X. Li, L. Song, D. Gao, B. Kang, G. Chen, Chem. Eur. J. 26 (2020) 4419-4424.
    [126]
    C. Han, P. Meng, E.R. Waclawik, C. Zhang, X.H. Li, H. Yang, M. Antonietti, J. Xu, Angew. Chem. Int. Ed. 57 (2018) 14857-14861.
    [127]
    Garima J., Vinod G. L., Murugan S., Ravishankar G. K., Radek Z., Manoj B. G., Ekambaram B., ACS Sustain. Chem. Eng. 8 (2020) 11058-11068.
    [128]
    Y. Liu, Q. Wang, L. Wu, Y. Long, J. Li, S. Song, H. Zhang, Nanoscale 11 (2019) 12932-12937.
    [129]
    K. Ganjehyan, B. Nisanci, M.S. Vim, A. Dastan, O. Metin, Appl. Organomet. Chem. 33 (2019) 4863.
    [130]
    L. Li, W. Yang, Q. Yang, Q. Guan, J. Lu, S.-H. Yu, H.-L. Jiang, ACS Catal. 10 (2020) 7753-7762.
    [131]
    C.E. Hartmann, V. Jurcik, O. Songis, C. Cazin, Chem. Commun. 49 (2013) 1005-1007.
    [132]
    J.K. Pagano, J. Stelmach, R. Waterman, Dalton Trans. 44 (2015) 12074-12077.
    [133]
    S. Fu, N.Y. Chen, X. Liu, Z. Shao, S.P. Luo, Q. Liu, J. Am. Chem. Soc. 138 (2016) 8588.
    [134]
    V.G. Landge, J. Pitchaimani, S.P. Midya, M. Subaramanian, V. Madhu, E. Balaraman, Catal. Sci. Technol. 8 (2018) 428-433.
    [135]
    Y.P. Zhou, Z. Mo, M.P. Luecke, M. Driess, Chem. Eur. J. 24 (2018) 4780 - 4784.
    [136]
    A. Brzozowska, L.M. Azofra, V. Zubar, I. Atodiresei, L. Cavallo, M. Rueping, O. El-Sepelgy, ACS Catal. 8 (2018) 4103-4109.
    [137]
    R. Barrios-Francisco, J.J. Garcia, Appl. Catal. A-Gen. 385 (2010) 108-113.
    [138]
    E. Korytiakova, N.O. Thiel, F. Pape, J.F. Teichert, Chem. Commun. 53 (2016) 732.
    [139]
    K.A. Erickson, J.P.W. Stelmach, N.T. Mucha, R. Waterman, Organometallics 34 (2015) 4693-4699.
    [140]
    X. Yang, T. Fox, H. Berke, Chem. Commun. 47 (2011) 2053-2055.
    [141]
    Che, Chang, Chong, P. Dr., Hajime, Hirao, And, P. Dr, Rei, Kinjo, Angew. Chem. 126 (2014) 3410-3414.
    [142]
    Y.-Y. Zhang, G.-W. Yang, R. Xie, L. Yang, B. Li, G.-P. Wu, Angew. Chem. Int. Edit. 59 (2020) 23291-23298.
    [143]
    G. Menard, D.W. Stephan, J. Am. Chem. Soc. 132 (2010) 1796-1797.
    [144]
    L. Roy, P.M. Zimmerman, A. Paul, Chem. Eur. J. 17 (2011) 435-439.
    [145]
    G. Menard, D.W. Stephan, Dalton Trans. 42 (2013) 5447-5453.
    [146]
    A. Jana, G. Tavcar, H.W. Roesky, M. John, Dalton Trans. 39 (2010) 9487-9489.
    [147]
    T.X. Zhao, G.W. Zhai, J. Liang, P. Li, X.B. Hu, Y.T. Wu, Chem. Commun. 53 (2017) 8046-8049.
    [148]
    T. Zhao, C. Li, X. Hu, F. Liu, Y. Wu, Int. J. Hydrogen Energ. 46 (2021) 15716-15723.
    [149]
    W. Yang, I.Y. Chernyshov, R.K.A. Van Schendel, M. Weber, C. Muller, G.A. Filonenko, E.A. Pidko, Nat. Commun. 12 (2021) 12.
    [150]
    Y. Zhou, Z. Li, Y. Liu, J. Huo, S. Wang, ChemSusChem 13 (2020) 1746 - 1750.
    [151]
    H.W. Kim, S. Byun, S.M. Kim, H.J. Kim, C. Lei, D.Y. Kang, A. Cho, B.M. Kim, J.K. Park, Catal. Sci. Technol. 10 (2020) 944-949.
    [152]
    Toeroek, Bela, Dastan, Arif, Ganjehyan, Khadijeh, Metin, Onder, Nisanci Bilal, J. Mole. Catal. A Chem. 409 (2015) 191-197.
    [153]
    P.V.R. A, P.D.G. A, K.S. A, P.C. B, Tetrahedron Lett. 51 (2010) 3167-3169.
    [154]
    L. Shi, Y. Liu, Q. Liu, B. Wei, G. Zhang, Cheminform 14 (2012) 1372-1375.
    [155]
    W. Xu, H. Fan, G. Wu, P. Chen, New J. Chem. 36 (2012).
    [156]
    N. Ma, M. Song, Q. Meng, C. Wei, G. Zhang, Int. J. Quantum Chem. 120 (2020) 26162.
    [157]
    W. Zhao, S. Meier, S. Yang, A. Riisager, Green Chem. 22 (2020) 5972-5977.
    [158]
    Q. Zhou, W. Meng, X. Feng, H. Du, J. Yang, Tetrahedron Lett. 61 (2020).
    [159]
    P.V. Ramachandran, S. Choudhary, A. Singh, J. Org. Chem. 86 (2021) 4274-4280.
    [160]
    X. Liu, L. Longwitz, B. Spiegelberg, J. Tonjes, T. Beweries, T. Werner, ACS Catal. 10 (2020) 13659-13667.
    [161]
    Y. Pan, C. Chen, X. Xu, H. Zhao, J. Han, H. Li, L. Xu, Q. Fan, J. Xiao, Green Chem. 20 (2018) 403-411.
    [162]
    M. Pang, J.Y. Chen, S. Zhang, R.Z. Liao, C.H. Tung, W. Wang, Nat. Commun. 11 (2020) 1249.
    [163]
    S. Li, W. Meng, H. Du, Org. Lett. 19 (2017) 2604-2606.
    [164]
    W. Zhao, Z. Zhang, X. Feng, J. Yang, H. Du, Org. Lett. 22 (2020) 5850-5854.
    [165]
    Q. Zhou, L. Zhang, W. Meng, X. Feng, J. Yang, H. Du, Org. Lett. 18 (2016) 5189-5191.
    [166]
    F. Ding, Y. Zhang, R. Zhao, Y. Jiang, R.L. Bao, K. Lin, L. Shi, Chem. Commun. 53 (2017) 9262-9264.
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