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Palladium carboxylate π-complexes with unsaturated hydrocarbons and the reactions catalyzed by them

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Abstract

This review summarizes the studies on the palladium carboxylate π-complexes with unsaturated hydrocarbons (alkenes, alkynes, and arenes) as well as with N-heterocyclic carbenes, phosphonyl-substituted ferrocene ligands, etc. In these complexes the palladium atoms are coordinated with unsaturated hydrocarbons via the carbon atoms forming the multiple bonds. These complexes are traditional objects in fundamental coordination chemistry including chemistry of polynuclear compounds. They are also applied as pre-catalysts and as model intermediates for catalytic transformations of unsaturated hydrocarbons, e.g., oxidation and isomerization of alkenes, hydrogenation and coupling reactions of alkenes, alkynes, and arenes.

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References

  1. M. P. Egorov, A. L. Maksimov, A. M. Muzafarov, N. E. Nifantiev, A. Yu. Tsivadge, Vestn. RAN [Herald Russ. Acad. Sci.], 2022, 92, 103; DOI: https://doi.org/10.31857/S0869587322020025 (in Russian).

    Google Scholar 

  2. S. P. Gubin, Khimiya klasterov. Osnovy klassifikatsii i stroeniya [Chemistry of Clusters: Basics of Classification and Structure], 2nd ed., URSS, Moscow, 2019, 264 pp. (in Russian).

    Google Scholar 

  3. A. N. Antsyshkina, O. I. Golyzhnikova, M. N. Vargaftik, G. G. Sadikov, V. N. Ostrikova, Ya. V. Salyn’, M. A. Porai-Koshits, I. I. Moiseev, Koord. Khim. [Russ. J. Coord. Chem.], 1980, 6, 1115 (in Russian).

    CAS  Google Scholar 

  4. K. S. Yang, J. A. Gurak, Z. Liu, K. M. Engle, J. Am. Chem. Soc., 2016, 138, 14705; DOI: https://doi.org/10.1021/jacs.6b08850.

    Article  CAS  PubMed  Google Scholar 

  5. Z. Liu, X. Li, T. Zeng, K. M. Engle, ACS Catal., 2019, 9, 3260; DOI: https://doi.org/10.1021/acscatal.9b00181.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  6. M. Liu, P. Yang, M. K. Karunananda, Y. Wang, P. Liu, K. M. Engle, J. Am. Chem. Soc., 2018, 140, 5805; DOI: https://doi.org/10.1021/jacs.8b02124.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  7. M. C. Gallazi, T. L. Hanlon, G. Vitulli, L. Porri, J. Organomet. Chem., 1971, 33, C45; DOI: https://doi.org/10.1016/S0022-328X(00)88395-3.

    Article  Google Scholar 

  8. M. Zocchi, G. Tieghi, A. Albinati, J. Organomet. Chem., 1971, 33, C47; DOI: https://doi.org/10.1016/S0022-328X(00)88396-5.

    Article  CAS  Google Scholar 

  9. M. Zocchi, G. Tieghi, A. Albinati, J. Chem. Soc., Dalton Trans., 1973, 883; DOI: https://doi.org/10.1039/DT9730000883.

  10. R. Giri, N. Maugel, B. M. Foxman, J.-Q. Yu, Organometallics, 2007, 27, 1667; DOI: https://doi.org/10.1021/om8000444.

    Article  Google Scholar 

  11. C. Bianchini, A. Meli, W. Oberhauser, A.M. Segarra, E. Passaglia, M. Lamač, P. Štčpnička, Eur. J. Inorg. Chem., 2008, 2008, 441; DOI: https://doi.org/10.1002/ejic.200700903.

    Article  Google Scholar 

  12. G. I. Dzhardimalieva, I. E. Uflyand, V. A. Zhinzhilo, Russ. Chem. Bull., 2022, 71, 2052; DOI: https://doi.org/10.1007/s11172-022-3628-6.

    Article  CAS  Google Scholar 

  13. T. A. Stromnova, D. V. Paschenko, L. I. Boganova, M. V. Daineko, S. B. Katser, A. V. Churakov, L. G. Kuz’mina, J. A. K. Howard, Inorg. Chim. Acta., 2003, 350, 284; DOI: https://doi.org/10.1016/S0020-1693(02)01575-X.

    Article  Google Scholar 

  14. T. A. Stromnova, M. V. Dayneko, A. V. Churakov, L. G. Kuz’mina, J. Cámpora, P. Palma, E. Carmona, Inorg. Chim. Acta., 2006, 359, 1613; DOI: https://doi.org/10.1016/j.ica.2005.11.037.

    Article  CAS  Google Scholar 

  15. R. E. Podobedov, T. A. Stromnova, A. V. Churakov, L. G. Kuz’mina, I. A. Efimenko, J. Organomet. Chem., 2010, 695, 2083; DOI: https://doi.org/10.1016/j.jorganchem.2010.05.019.

    Article  CAS  Google Scholar 

  16. O. N. Shishilov, R. E. Podobedov, Ya. N. Rezinkova, A. V. Churakov, I. A. Efimenko, Dalton Trans., 2013, 42, 1338; DOI: https://doi.org/10.1039/C2DT31824E.

    Article  CAS  PubMed  Google Scholar 

  17. T. A. Stromnova, K. Yu. Monakhov, J. Cámpora, P. Palma, E. Carmona, E. Alvarez, Inorg. Chim. Acta., 2007, 360, 4111; DOI: https://doi.org/10.1016/j.ica.2007.05.058.

    Article  CAS  Google Scholar 

  18. O. N. Shishilov, P. V. Ankudinova, E. V. Nikitenko, A. V. Churakov, I. A. Garbuzova, N. S. Akhmadullina, N. A. Minaeva, L. I. Demina, I. A. Efimenko, J. Organomet. Chem., 2014, 767, 112; DOI: https://doi.org/10.1016/j.jorganchem.2014.05.011.

    Article  CAS  Google Scholar 

  19. I. A. Efimenko, O. S. Erofeeva, E. A. Ugolkova, N. N. Efimov, L. I. Demina, P. V. Grishanova, V. V. Minin, Mendeleev Commun., 2018, 28, 632; DOI: https://doi.org/10.1016/j.mencom.2018.11.023.

    Article  CAS  Google Scholar 

  20. I. I. Moiseev, E. A. Federovskaya, Ya. K. Syrkin, Zh. Neorg. Khim. [J. Inorg. Chem. USSR], 1959, 4, 2641 (in Russian).

    CAS  Google Scholar 

  21. J. Smidt, W. Hafner, Angew. Chem., 1959, 71, 284; DOI: https://doi.org/10.1002/ange.19590710809.

    Article  ADS  CAS  Google Scholar 

  22. M. S. Lupin, S. D. Robinson, B. L. Shaw, Proc. 8th Int. Conf. on Coordination Chemistry (Vienne, September 7–11, 1964), Vienne, 1964, 223; DOI: https://doi.org/10.1007/978-3-7091-3650-8.

  23. M. R. Churchill, R. Mason, Nature, 1964, 204, 777; DOI: https://doi.org/10.1038/204777a0.

    Article  ADS  CAS  Google Scholar 

  24. E. Benedetti, G. Maglio, R. Palumbo, C. Pedone, J. Organomet. Chem., 1973, 60, 189; DOI: https://doi.org/10.1016/S0022-328X(00)85450-9.

    Article  CAS  Google Scholar 

  25. J. N. Jaworski, C. V. Kozack, S. J. Tereniak, S. M. M. Knapp, C. R. Landis, J. T. Miller, S. S. Stahl, J. Am. Chem. Soc., 2019, 141, 10462; DOI: https://doi.org/10.1021/jacs.9b04699.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  26. M. H. Katcher, P.-O. Norrby, A. G. Doyle, Organometallics, 2014, 33, 2121; DOI: https://doi.org/10.1021/om401240p.

    Article  CAS  Google Scholar 

  27. L. Bettuccia, C. Bianchinia, W. Oberhausera, T.-H. Hsiaob, H. M. Leeb, J. Mol. Catal. A: Chem., 2010, 322, 63; DOI: https://doi.org/10.1016/j.molcata.2010.02.016.

    Article  Google Scholar 

  28. M. A. Topchij, A. A. Ageshina, S. A. Rzhevskij, L. I. Minaeva, M. S. Nechaev, A. F. Asachenko, Russ. Chem. Bull., 2022, 71, 940; DOI: https://doi.org/10.1007/s11172-022-3494-2.

    Article  Google Scholar 

  29. R. G. Brown, R. V. Chaudhari, J. M. Davidson, J. Chem. Soc., Dalton Trans., 1977, 176; DOI: https://doi.org/10.1039/DT9770000176.

  30. V. K. Jain, L. Jain, Coord. Chem. Rev., 2010, 254, 2848; DOI: https://doi.org/10.1016/j.ccr.2010.05.010.

    Article  CAS  Google Scholar 

  31. A. Behr, G. V. Ilsemann, W. Keim, C. Krueger, Y. H. Tsay, Organometallics, 1986, 5, 514; DOI: https://doi.org/10.1021/om00134a020.

    Article  CAS  Google Scholar 

  32. G. J. P. Britovsek, W. Keim, S. Mecking, D. Sainzb, T. Wagner, J. Chem. Soc., Chem. Commun., 1993, 1632; DOI: https://doi.org/10.1039/C39930001632.

  33. C. Melero, O. N. Shishilov, E. Álvarez, P. Palma, J. Cámpora, Dalton Trans., 2012, 41, 14087; DOI: https://doi.org/10.1039/C2DT31728A.

    Article  CAS  PubMed  Google Scholar 

  34. P. L. Ruddock, D. J. Williams, P. B. Reese, Steroids, 2004, 69, 193; DOI: https://doi.org/10.1016/j.steroids.2004.01.001.

    Article  CAS  PubMed  Google Scholar 

  35. S. Y. Lee, J. F. Hartwig, J. Am. Chem. Soc., 2016, 138, 15278; DOI: https://doi.org/10.1021/jacs.6b10220.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  36. I. Schwarz, J. Rust, C. W. Lehmann, M. Braun, J. Organomet. Chem., 2000, 605, 109; DOI: https://doi.org/10.1016/S0022-328X(00)00276-X.

    Article  CAS  Google Scholar 

  37. P. Štěpnička, I. Císařová, Coll. Czech. Chem. Comm., 2006, 71, 279; DOI: https://doi.org/10.1135/cccc20060279.

    Article  Google Scholar 

  38. E. Benedetti, G. Maglio, R. Palumbo, C. Pedone, J. Organomet. Chem., 1973, 60, 189; DOI: https://doi.org/10.1016/S0022-328X(00)85450-9.

    Article  CAS  Google Scholar 

  39. E. Schuhmann, C. Robl, W. Beck, Z. Naturforsch. B., 1994, 49b, 1569; DOI: https://doi.org/10.1515/znb-1994-1120.

    Article  Google Scholar 

  40. R. Czarnomysy, D. Radomska, O. K. Szewczyk, P. Roszczenko, K. Bielawski, Int. J. Mol. Sci., 2021, 22, 8271; DOI: https://doi.org/10.3390/jjms22158271.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  41. A. M. Allgeier, B. J. Shaw, T.-L. Hwang, J. E. Milne, J. S. Tedrow, C. N. Wilde, Organometallics, 2012, 31, 519; DOI: https://doi.org/10.1021/om200988f.

    Article  CAS  Google Scholar 

  42. L. Yu, Ukhin, N. A. Dolgopolova, L. G. Kuz’mina, Yu. T. Struchkov, J. Organomet. Chem., 1981, 210, 263; DOI: https://doi.org/10.1016/S0022-328X(00)82238-X.

    Article  Google Scholar 

  43. I. A. Efimenko, R. E. Podobedov, O. N. Shishilov, Ya. N. Rezinkova, A. V. Churakov, L. G. Kuz’mina, I. G. Garbuzova, B. V. Lokshin, Inorg. Chem. Commun., 2011, 14, 426; DOI: https://doi.org/10.1016/j.inoche.2010.12.018.

    Article  CAS  Google Scholar 

  44. D. P. Hruszkewycz, J. Wu, N. Hazari, C. D. Incarvito, J. Am. Chem. Soc., 2011, 133, 3280; DOI: https://doi.org/10.1021/ja110708k.

    Article  CAS  PubMed  Google Scholar 

  45. D. P. Hruszkewycz, J. Wu, J. C. Green, N. Hazari, T. J. Schmeier, Organometallics, 2012, 31, 470; DOI: https://doi.org/10.1021/om201163k.

    Article  CAS  Google Scholar 

  46. J. Wu, J. C. Green, N. Hazari, D. P. Hruszkewycz, C. D. Incarvito, T. J. Schmeier, Organometallics, 2010, 29, 6369; DOI: https://doi.org/10.1021/om1007456.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  47. M. Kořenková, M. Hejda, R. Jirásko, T. Block, F. Uhlík, R. Jambor, A. Růžička, R. Pöttgenc, L. Dostál, Dalton Trans., 2019, 48, 11912; DOI: https://doi.org/10.1039/C9DT02340B.

    Article  PubMed  Google Scholar 

  48. K. A. Kozhanov, V. K. Cherkasov, M. P. Bubnov, Russ. Chem. Bull., 2022, 71, 1527; DOI: https://doi.org/10.1007/s11172-022-3560-9.

    Article  CAS  Google Scholar 

  49. M. V. Dayneko, T. A. Stromnova, L. S. Alekseev, R. S. Shamsiev, A. P. Belov, D. I. Kochubei, B. N. Novgorodov, Russ. J. Inorg. Chem., 2005, 50, 365.

    Google Scholar 

  50. R. E. Podobedov, T. A. Stromnova, Russ. J. Coord. Chem., 2008, 34, 780; DOI: https://doi.org/10.1134/S1070328408100138.

    Article  CAS  Google Scholar 

  51. R. E. Podobedov, T. A. Stromnova, I. P. Stolyarov, Russ. Chem. Bull., 2010, 59, 473; DOI: https://doi.org/10.1007/s11172-010-0105-4.

    Article  CAS  Google Scholar 

  52. Y. Li, W.-H. Wang, K.-H. He, Zh.-J. Shi, Organometallics, 2012, 31, 4397; DOI: https://doi.org/10.1021/om300284t.

    Article  CAS  Google Scholar 

  53. K. Yu. Monakhov, C. Gourlaouen, P. Braunstein, Chem. Commun., 2012, 48, 8317; DOI: https://doi.org/10.1039/C2CC32886K.

    Article  CAS  Google Scholar 

  54. M. Catellani, G. Chiusoli, E. Dradi, G. Salerno, J. Organomet. Chem., 1979, 177, C29; DOI: https://doi.org/10.1016/S0022-328X(00)94094-4.

    Article  CAS  Google Scholar 

  55. U. M. Dzhemilev, R. I. Khusnutdinov, D. K. Galeev, O. M. Nefedov, G. A. Tolstikov, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1987, 36, 122; DOI: https://doi.org/10.1007/BF00953861.

    Article  Google Scholar 

  56. U. M. Dzhemilev, R. I. Khusnutdinov, D. K. Galeev, G. A. Tolstikov, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1987, 36, 136; DOI: https://doi.org/10.1007/BF00953863.

    Google Scholar 

  57. N. Tsukada, T. Sato, Y. Inoue, Tetrahedron Lett., 2000, 41, 4181; DOI: https://doi.org/10.1016/S0040-4039(00)00600-6.

    Article  CAS  Google Scholar 

  58. S. V. Leont’eva, O. S. Manulik, E. M. Evstigneeva, E. N. Bobkova, V. R. Flid, Kinet. Catal., 2006, 47, 384; DOI: https://doi.org/10.1134/S0023158406030098.

    Article  Google Scholar 

  59. I. P. Stolyarov, A. E. Gekhman, I. I. Moiseev, A. Yu. Kolesnikov, E. M. Evstigneeva, V. R. Flid, Russ. Chem. Bull., 2007, 56, 320; DOI: https://doi.org/10.1007/s11172-007-0052-x.

    Article  CAS  Google Scholar 

  60. E. M. Evstigneeva, O. S. Manulik, V. R. Flid, Kinet. Catal., 2004, 45, 172; DOI: https://doi.org/10.1023/B:KICA.0000023787.79493.e7.

    Article  CAS  Google Scholar 

  61. V. R. Flid, M. L. Gringolts, R. S. Shamsiev, E. Sh. Finkelshtein, Russ. Chem. Rev., 2018, 87, 1169; DOI: https://doi.org/10.1070/RCR4834.

    Article  ADS  CAS  Google Scholar 

  62. Z. Li, J. Zheng, C. Li, W. Wu, H. Jiang, Chin. J. Chem., 2019, 37, 140; DOI: https://doi.org/10.1002/cjoc.201800536

    Article  CAS  Google Scholar 

  63. V. R. Flid, S. A. Durakov, T. A. Morozova, Russ. Chem. Bull., 2016, 65, 2639; DOI: https://doi.org/10.1007/s11172-016-1629-z.

    Article  CAS  Google Scholar 

  64. R. S. Shamsiev, V. R. Flid, Russ. Chem. Bull., 2020, 69, 653; DOI: https://doi.org/10.1007/s11172-020-2813-8.

    Article  CAS  Google Scholar 

  65. E. M. Evstigneeva, O. S. Manulik, V. R. Flid, I. P. Stolyarov, N. Yu. Kozitsyna, M. N. Vargaftik, I. I. Moiseev, Russ. Chem. Bull., 2004, 53, 1345; DOI: https://doi.org/10.1023/B:RUCB.0000042298.81687.dd.

    Article  CAS  Google Scholar 

  66. S. A. Durakov, R. S. Shamsiev, V. R. Flid, A. E. Gekhman, Kinet. Catal., 2019, 60, 245; DOI: https://doi.org/10.1134/S0023158419030042.

    Article  CAS  Google Scholar 

  67. E. M. Evstigneeva, V. R. Flid, Russ. Chem. Bull., 2008, 57, 837; DOI: https://doi.org/10.1007/s11172-008-0121-9.

    Article  CAS  Google Scholar 

  68. V. R. Flid, O. S. Manulik, A. P. Belov, A. A. Grigor’ev, Metalloorg. Khim. [Organomet. Chem.], 1991, 4, 864 (in Russian).

    CAS  Google Scholar 

  69. S. A. Durakov, R. S. SHamsiev, V. R. Flid, A. E. Gekhman, Russ. Chem. Bull., 2018, 67, 2234; DOI: https://doi.org/10.1007/s11172-018-2361-7.

    Article  CAS  Google Scholar 

  70. Y. Chen, J. P. Romarie, T. R. Newhouse, J. Am. Chem. Soc., 2015, 137, 5875; DOI: https://doi.org/10.1021/jacs.5b02243.

    Article  CAS  PubMed  Google Scholar 

  71. N. Miyaura, Cross-Coupling Reactions: A Practical Guide, Springer, Berlin, 2002, pp. 212–237; ISBN 978-3-540-42175-7.

    Book  Google Scholar 

  72. F. Diederich, P. J. Stang, Metal-Catalyzed Cross-Coupling Reactions (Chs 2–7, 9, 11), Wiley-VCH, Weinheim, Germany, 2008.

    Google Scholar 

  73. N. Miyaura, A. Suzuki, Chem. Rev., 1995, 95, 2457; DOI: https://doi.org/10.1021/cr00039a007.

    Article  CAS  Google Scholar 

  74. A. Suzuki, Angew. Chem., Int. Ed., 2011, 50, 6722; DOI: https://doi.org/10.1002/anie.201101379.

    Article  CAS  Google Scholar 

  75. X.-S. Zhang, Y.-F. Zhang, Z.-W. Li, F.-X. Luo, Z.-J. Shi, Angew. Chem. Int. Ed., 2015, 54, 5478; DOI: https://doi.org/10.1002/anie.201500486.

    Article  CAS  Google Scholar 

  76. S. Yang, R. Cheng, T. Zhao, A. Luo, J. Lan, J. You, Org. Lett., 2019, 21, 5086; DOI: https://doi.org/10.1021/acs.orglett.9b01679.

    Article  CAS  PubMed  Google Scholar 

  77. Z. She, Y. Wang, D. Wang, Y. Zhao, T. Wang, X. Zheng, Z.-X. Yu, G. Gao, J. You, J. Am. Chem. Soc., 2018, 140, 12566; DOI: https://doi.org/10.1021/jacs.8b07485.

    Article  CAS  PubMed  Google Scholar 

  78. Y. Ran, Y. Yang, H. You, J. You, ACS Catal., 2018, 8, 1796; DOI: https://doi.org/10.1021/acscatal.7b04298.

    Article  CAS  Google Scholar 

  79. L. Zhang, L. Zhu, Y. Zhang, Y. Yang, Y. Wu, W. Ma, Y. Lan, J. You, ACS Catal., 2018, 8, 8324; DOI: https://doi.org/10.1021/acscatal.8b02816.

    Article  CAS  Google Scholar 

  80. W. V. Konze, B. L. Scott, G. J. Kubas, J. Am. Chem. Soc., 2002, 124, 12550; DOI: https://doi.org/10.1021/ja020798h.

    Article  CAS  PubMed  Google Scholar 

  81. T. Calvet, M. Crespo, M. Font-Bardia, K. Gómez, G. González, M. Martínez, Organometallics, 2009, 28, 5096; DOI: https://doi.org/10.1021/om9004934.

    Article  CAS  Google Scholar 

  82. A. Kar, N. Mangu, H. M. Kaiser, M. Beller, M. K. Tse, Chem. Commun., 2008, 386; DOI: https://doi.org/10.1039/B714928J.

  83. X. C. Cambeiro, N. Ahlsten, I. Larrosa, J. Am. Chem. Soc., 2015, 137, 15636; DOI: https://doi.org/10.1021/jacs.5b10593.

    Article  CAS  PubMed  Google Scholar 

  84. H.-Q. Do, O. Daugulis, Chem. Commun., 2009, 6433; DOI: https://doi.org/10.1039/B912890E.

  85. N. Lv, Z. Chen, Y. Liu, Z. Liu, Y. Zhang, Org. Lett., 2018, 20, 5845; DOI: https://doi.org/10.1021/acs.orglett.8b02526.

    Article  CAS  PubMed  Google Scholar 

  86. D. Wang, Y. Izawa, S. S. Stahl, J. Am. Chem. Soc., 2014, 136, 9914; DOI: https://doi.org/10.1021/ja505405u.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  87. O. N. Shishilov, R. S. Shamsiev, N. S. Akhmadullina, V. R. Flid, ChemistrySelect., 2020, 5, 1080; DOI: https://doi.org/10.1002/slct.201904452.

    Article  CAS  Google Scholar 

  88. O. N. Shishilov, R. S. Shamsiev, N. S. Akhmadullina, V. R. Flid, ChemistrySelect., 2021, 6, 1795; DOI: https://doi.org/10.1002/slct.202004191.

    Article  CAS  Google Scholar 

  89. I. Funes-Ardoiz, F. Maseras, ACS Catal., 2018, 8, 1161; DOI: https://doi.org/10.1021/acscatal.7b02974.

    Article  CAS  Google Scholar 

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This work was financially supported by the Russian Science Foundation (Project No. 23-73-00123).

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Dedicated to Academician of the Russian Academy of Sciences M. P. Egorov on the occasion of his 70th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 73, No. 2, pp. 297–327, February, 2024.

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Shishilov, O.N., Durakov, S.A., Akhmadullina, N.S. et al. Palladium carboxylate π-complexes with unsaturated hydrocarbons and the reactions catalyzed by them. Russ Chem Bull 73, 297–327 (2024). https://doi.org/10.1007/s11172-024-4139-4

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