Kinetics and Mechanism of Aerobic Oxidation of Alcohols in the Presence of Palladium Carboxylate Complexes. A Review

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The paper examines the kinetics and mechanism of aerobic oxidation of alcohols in the presence of various types of palladium carboxylate complexes, including binary carboxylates Pd(RCO2)2, complexes containing N-heterocyclocarboxylic acid anions, palladium nitrosyl carboxylates Pd4(NO)2(RCO2)4, and also summarizes the currently available information on the direct interaction of palladium carboxylate complexes with alcohols.

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作者简介

O. Shishilov

MIREA – Russian Technological University

编辑信件的主要联系方式.
Email: oshishilov@gmail.com
俄罗斯联邦, Moscow

V. Polyakova

MIREA – Russian Technological University

Email: oshishilov@gmail.com
俄罗斯联邦, Moscow

N. Akhmadullina

A.A. Baikov Institute of Metallurgy and Material Science of the Russian Academy of Sciences

Email: oshishilov@gmail.com
俄罗斯联邦, Moscow

R. Shamsiev

MIREA – Russian Technological University

Email: oshishilov@gmail.com
俄罗斯联邦, Moscow

V. Flid

MIREA – Russian Technological University

Email: oshishilov@gmail.com
俄罗斯联邦, Moscow

参考

  1. Stahl S.S. // Angew. Chem. Int. Ed. 2004. V. 43. P. 3400.
  2. Zeni G., Larock R.C. // Chem. Rev. 2004. V. 104. P. 2285.
  3. Sigman M.S., Jensen D.R. // Acc. Chem. Res. 2006. V. 39. P. 221.
  4. Beccalli E.M., Broggini G., Martinelli M., Sottocornola S. // Chem. Rev. 2007. V. 107. P. 5318.
  5. Minatti A., Muñiz K. // Chem. Soc. Rev. 2007. V. 36. P. 1142.
  6. Karimi B., Zamani A. // J. Iran. Chem. Soc. 2008. V. 5. P. S1.
  7. Chen X., Engle K.M., Wang D.-H., Yu J.-Q. // Angew. Chem. Int. Ed. 2009. V. 49. P. 5094.
  8. Yeung C.S., Dong V.M. // Chem. Rev. 2011. V. 111. P. 1215.
  9. Liu C., Zhang H., Shi W., Lei A. // Chem. Rev. 2011. V. 111. P. 1780.
  10. McDonald R.I., Liu G., Stahl S.S. // Chem. Rev. 2011. V. 111. P. 2981.
  11. Liron F., Oble J., Lorion M.M., Poli G. // Eur. J. Org. Chem. 2014. P. 5863.
  12. Wang D., Weinstein A.B., White P.B., Stahl S.S. // Chem. Rev. 2018. V. 118. P. 2636.
  13. Курохтина А.А., Ларина Е.В., Лагода Н.А., Шмидт А.Ф. // Кинетика и катализ. 2022. Т. 63. № 5. С. 614.
  14. Тёмкин О.Н. // Кинетика и катализ. 2023. Т. 64. № 5. С. 528.
  15. Костюкович А.Ю., Патиль Е.Д., Бурыкина Ю.В., Анаников В.П. // Кинетика и катализ. 2023. Т. 64. № 1. С. 53.
  16. Hudlicky M. Oxidations in Organic Chemistry. American Chemical Society, Washington DC, 1990.
  17. Tojo G., Fernández M. Oxidation of Alcohol to Aldehydes and Ketones: A Guide to Common Practice. New York: Springer, 2006.
  18. Sheldon R.A. // Chem. Soc. Rev. 2012. V. 41. P. 1437.
  19. Modern Oxidation Methods. Ed. Bäckvall J.E. Winheim: Wiley-VCH, 2004.
  20. Punniyamurthy T., Velusamy S., Iqbal J. // Chem. Rev. 2005. V. 105. P. 2329.
  21. Schultz M.J., Sigman M.S. // Tetrahedron. 2006. V. 62. P. 8227.
  22. Berzelius J.J. // Pogg. Ann. 1828. V. 13. P. 435.
  23. Tsuji J. Paladium Reagents and Catalysts. New Perspectives for the 21st Centruy. Chichester. U.K.: J. Wiley & Sons, 2004.
  24. Jira R. // Angew. Chem. Int. Ed. 2009. V. 48. P. 9034.
  25. Keith J.A., Henry P.M. // Angew. Chem. Int. Ed. 2009. V. 48. P. 9038.
  26. Stahl S.S. // Science. 2005. V. 309. P. 1824.
  27. Stephenson T.A., Morehouse S.M., Powell A.R., Heffer J.P., Wilkinson G. // J. Chem. Soc. 1965. P. 3632.
  28. Бацанов А.С., Тимко Г.А., Стручков Ю.Т., Гэрбэлэу Н.В., Индричан К.М., Попович Г.А. // Коорд. химия. 1989. Т. 15. № 5. С. 688.
  29. Bancroft D.P., Cotton F.A., Falvello L.R., Schwotzer W. // Polyhedron. V. 7. № 8. P. 615.
  30. Козицына Н.Ю., Мартенс М.В., Столяров И.П., Нефедов С.Е., Варгафтик М.Н., Еременко И.Л., Моисеев И.И. // Журн. неорг. химии. 1999. Т. 44. № 11. С. 1915.
  31. Ефименко И.А., Подобедов Р.Е., Чураков А.В., Кузьмина Л.Г., Гарбузова И.А., Локшин Б.В., Максимов А.Л., Флид В.Р. // Коорд. химия. 2011. Т. 37. № 8. С. 625.
  32. Stromnova T.A., Monakhov K.Yu., Campora J., Palma P., Carmona E., Alvarez E. // Inorg. Chim. Acta. 2007. V. 360. P. 4111.
  33. Willcox D., Chappell B.G.N., Hogg K.F., Calleja J., Smalley A.P., Gaunt M.J. // Science. 2016. V. 354. P. 851.
  34. Moiseev I.I., Stromnova T.A., Vargaftik M.N., Mazo G. Ja., Kuz'mina L.G., Struchkov Yu.T. // J. Chem. Soc., Chem. Commun. 1978. V. 1. P. 27.
  35. Stromnova T.A., Shishilov O.N., Dayneko M.V., Monakhov K.Yu., Churakov A.V., Kuz’mina L.G., Howard J.A.K. // J. Organomet. Chem. 2006. V. 691. P. 3730.
  36. Shishilov O.N., Ankudinova P.V., Nikitenko E.V., Churakov A.V., Garbuzova I.A., Akhmadullina N.S., Minaeva N.A., Demina L.I., Efimenko I.A. // J. Organomet. Chem. 2014. V. 767. P. 112.
  37. Kirik S.D., Mulagaleev R.F., Blokhin A.I. // Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 2004. V. C60. P. m449.
  38. Marson A., van Oort A.B., Mul W.P. // Eur. J. Inorg. Chem. 2002. P. 3028.
  39. Bakhmutov V.I., Berry J.F., Cotton F.A., Ibragimov S., Murillo C.A. // Dalton Trans. 2005. Р. 1989.
  40. Bianchini C., Meli A., Oberhauser W. // Organometallics. 2003. V. 22. P. 4281.
  41. Zagorodnikov V.P., Ryabov A.D., Yatsimirskii A.K. // Kinet. Сatal. 1981. V. 22. P. 132.
  42. Khabibulin V.R., Kulik A.V., Oshanina I.V., Bruk L.G., Temkin O.N., Nosova V.M., Ustynyuk Yu.A., Bel’skii V.K., Stash A.I., Lysenko K.A., Antipin M.Yu. // Kinet. Catal. 2007. V. 48. P. 228.
  43. Nosova V.M., Ustynyuk Yu.A., Bruk L.G., Temkin O.N., Kisin A.V., Storozhenko P.A. // Inorg. Chem. 2011. V. 50. P. 9300.
  44. Bedford R.B., Bowen J.G., Davidson R.B., Haddow M.F., Seymour-Julen A.E., Sparkes H.A., Webster R.L. // Angew. Chem. Int. Ed. 2015. V. 54. № 22. P. 6591.
  45. Stromnova T.A., Paschenko D.V., Boganova L.I., Daineko M.V., Katser S.B., Churakov A.V., Kuz’mina L.G., Howard J.A.K. // Inorg. Chim. Acta. 2003. V. 350. P. 283.
  46. Shishilov O.N., Stromnova T.A., Efimenko I.A., Churakov A.V., Howard J.A.K., Minaeva N.A. // J. Organomet. Chem. 2011. P. 2023.
  47. Shishilov O.N., Akhmadullina N.S., Rezinkova Ya.N., Podobedov R.E., Churakov A.V., Efimenko I.A. // Dalton Trans. 2013. V. 42. P. 3712.
  48. Shishilov O.N., Shamsiev R.S., Akhmadullina N.S., Naumova V.A., Flid V.R. // J. Mol. Struct. 2018. V. 1173. P. 974.
  49. Jira R. // Angew. Chem. Int. Ed. 2009. V. 48. № 48. P. 9034.
  50. Keith J.A., Henry P.M. // Angew. Chem. Int. Ed. 2009. V. 48. P. 9038.
  51. Gilgorich K.M., Sigman M.S. // Chem. Commun. 2009. P. 3854.
  52. Peterson K.P., Larock R.C. // J. Org. Chem. 1998. V. 63. № 10. P. 3185.
  53. Nishimura T., Onoue T., Ohe K., Uemura S. // J. Org. Chem. 1999. V. 64. № 18. P. 6750.
  54. Schultz M.J., Park C.C., Sigman M.S. // Chem. Commun. 2002. P. 3034.
  55. Schultz M.J., Hamilton S.S., Jensen D.R., Sigman M.S. // J. Org. Chem. 2005. V. 70. № 9. P. 3343.
  56. Steinhoff B.A., Fix S.R., Stahl S.S. // J. Am. Chem. Soc. 2002. V. 124. № 5. P. 766.
  57. Steinhoff B.A., Guzei I.A., Stahl S.S. // J. Am. Chem. Soc. 2004. V. 126. № 36. P. 11268.
  58. Schultz M.J., Adler R.S., Zierkiewicz W., Privalov T., Sigman M.S. // J. Am. Chem. Soc. 2005. V. 127. P. 8499.
  59. ten Brink G.-J., Papadogianakis G., Arends I.W.C.E., Sheldon R.A. // Appl. Catal. A: Gen. 2000. V. 194–195. P. 435.
  60. ten Brink G.-J., Arends I.W.C.E., Sheldon R.A. // Science. 2001. V. 287. № 5458. P. 1636.
  61. ten Brink G.-J., Arends I.W.C.E., Hoogenraad M., Verspui G., Sheldon R.A. // Adv. Synth. Catal. 2003. V. 345. P. 1341.
  62. ten Brink G.-J., Arends I.W.C.E., Hoogenraad M., Verspui G., Sheldon R.A. // Adv. Synth. Catal. 2003. V. 345. P. 497.
  63. Jensen D.R., Pugsley J.S., Sigman M.S. // J. Am. Chem. Soc. 2001. V. 123. № 30. P. 7475.
  64. Ferreira E.M., Stoltz B.M. // J. Am. Chem. Soc. 2001. V. 123. № 31. P. 7725.
  65. Jensen D.R., Schulz M.J., Mueller J.A., Sigman M.S. // Angew. Chem. Int. Ed. 2003. V. 42. № 32. P. 3810.
  66. Paavola S., Zatterberg K., Privalov T., Csöregh I., Moberg C. // Adv. Synth. Catal. 2004. V. 346. № 2–3. P. 237.
  67. Urgoitia G., SanMartin R., Herrero M.T., Domínguez E. // Green Chem. 2011. V. 13. P. 2161.
  68. Pearson D.M., Conley N.R., Waymouth R.M. // Organometallics. 2011. V. 30. № 6. P. 1445.
  69. ten Brink G.-J., Arends I.W.C.E., Sheldon R.A. // Adv. Synth. Catal. 2002. V. 344. № 3–4. P. 355.
  70. Steinhoff B.A., Stahl S.S. // J. Am. Chem. Soc. 2006. V. 128. № 13. P. 4348.
  71. Trend R.M., Stoltz B.M. // J. Am. Chem. Soc. 2004. V. 126. № 14. P. 4482.
  72. Trend R.M., Stoltz B.M. // J. Am. Chem. Soc. 2008. V. 130. № 47. P. 15957.
  73. Ebner D.C., Bagdanoff J.T., Ferreira E.M., McFadden R.M., Caspi D.C., Trend R.M., Stoltz B.M. // Chem. Eur. J. 2009. V. 15. № 47. P. 12978.
  74. Privalov T., Linde C., Zatterberg K., Moberg C. // Organometallics. 2005. V. 24. № 5. P. 885.
  75. Stahl S.S., Thorman J.L., Nelson R.C., Kozee M.A. // J. Am. Chem. Soc. 2001. V. 123. № 29. P. 7188.
  76. Konnick M.M., Guzel I.A., Stahl S.S. // J. Am. Chem. Soc. 2004. V. 126. № 33. P. 10212.
  77. Popp B.V., Wendlandt J.E., Landis C.R., Stahl S.S. // J. Am. Chem. Soc. 2007. V. 129. № 3. P. 601.
  78. Keith J.M., Nielsen R.J., Oxgaard J., Goddard W.A. // J. Am. Chem. Soc. 2005. V. 127. № 38. P. 13172.
  79. Denney M.C., Smythe N.A., Cetto K.L., Kemp R.A., Goldberg K.I. // J. Am. Chem. Soc. 2006. V. 128. № 8. P. 2058.
  80. Keith J.M., Muller R.P., Kemp R.A., Goldberg K.I., Goddard W.A., Oxgaard J. // Inorg. Chem. 2006. V. 45. № 24. P. 9631.
  81. Keith J.M., Goddard W.A. // J. Am. Chem. Soc. 2009. V. 131. № 4. P. 1416.
  82. Popp B.V., Stahl S.S. // J. Am. Chem. Soc. 2007. V. 129. № 14. P. 4410.
  83. Popp B.V., Stahl S.S. // Chem. Eur. J. 2009. V. 15. № 12. P. 2915.
  84. Bianchi D., Bortolo R., D'Aloisio R., Ricci M. // Angew. Chem. Int. Ed. 1999. V. 38. № 5. P. 706.
  85. Steinhoff B.A., King A.E., Stahl S.S. // J. Org. Chem. 2006. V. 71. № 5. P. 1861.
  86. Mueller J.A., Jensen D.R., Sigman M.S. // J. Am. Chem. Soc. 2002. V. 124. № 28. P. 8202.
  87. Bettucci L., Bianchini C., Filippi J., Lavacchi A., Overhauser W. // Eur. J. Inorg. Chem. 2011. № 11. P. 1797.
  88. Zhao J., Hasslink H., Hartwi J.F. // J. Am. Chem. Soc. 2001. V. 123. № 30. P. 7220.
  89. Macgregor S.A., Vadivelhu P. // Organometallics. 2007. V. 26. № 15. P. 3651.
  90. Zhao H., Ariafard A., Lin Z. // Organometallics. 2006. V. 25. № 4. P. 812.
  91. Theofanis P.L., Goddard R.A. // Organometallics. 2011. V. 30. № 18. P. 4941.
  92. Farfard C.M., Ozerov O.V. // Inorg. Chim. Acta. 2007. V. 360. P. 286.
  93. Melero C., Martínez-Prieto L.M., Palma P., del Río D., Álvarez E., Cámpora J. // Chem. Commun. 2010. V. 46. P. 8851.
  94. Schultz M.J., Hamilton S.S., Jensen D.R., Sigman M.S. // J. Org. Chem. 2005. V. 70. P. 3343.
  95. Conley N.R., Labios L.A., Pearson D.M., McCrory C.L.C., Waymouth R.M. // Organometallics. 2007. V. 56. № 23. P. 5447.
  96. Melero C., Shishilov O.N., Alvarez E., Palma P., Campora J. // Dalton Trans. 2012. V. 41. P. 14087.
  97. Urry W.H., Kharasch M.S. // J. Am. Chem. Soc. 1944. V. 66. № 9. P. 1438.
  98. Studer A., Bossart M. // Tetrahedron. 2001. V. 57. P. 9649.
  99. Boisvert L., Denney M.C., Kloek Hanson S., Goldberg K. // J. Am. Chem. Soc. 2009. V. 131. № 43. P. 15802.
  100. Huacuja R., Graham D.J., Farfard C.M., Chen C.-H., Foxman B.M., Herbert D.E., Allinger G., Thomas C.M., Ozerov O.V. // J. Am. Chem. Soc. 2011. V. 133. № 11. P. 3820.
  101. Traubmann S., Alt H.G. // J. Mol. Catal. A: Chem. 2008. V. 289. P. 44.
  102. Шмидт А.Ф., Курохтина А.А., Ларина Е.В., Лагода Н.А. // Тонкие химические технологии. 2023. Т. 18. № 4. С. 328.

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2. Fig. 1. Structure of Pd3(RCO2)6 (a), Pd4(CO)4(RCO)4 (b), Pd6(CO)6(RCO2)6 (c) and catena-[Pd(OAc)2]n (d) complexes

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3. Fig. 2. Structure of Pd3(μ-OMe)(μ-OAc)5 (a), Pd3(μ-OMe)2(OAc)4 (b) and Pd3(μ-OH)(μ-OAc)5 (c) complexes

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4. Fig. 3. Structure of palladium nitrosyl carboxylates Pd4(μ-NO)2(μ-RCO2)6 (a) and Pd4(μ-NO)4(μ-RCO2)4 (b)

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5. Fig. 4. Possible pathways of transformation of Pd4(NO)2(OAc)6 into Pd2(NO)(OAc)3(MeOH)2 in the presence of methanol according to DFT calculations

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6. Fig. 5. Possible route of transformation of Pd2(NO)(OAc)3(MeOH)2 to Pd(NO)(OAc)(MeOH)3 and Pd(OAc)2(MeOH)2 in the presence of methanol

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7. Scheme 1. Generalised mechanism of alcohol oxidation in the presence of palladium complexes

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8. Scheme 2. Synthesis of neophilic palladium complexes containing N-heterocyclocarboxylic and sulfonic acid residues and N- and P-donor ligands

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9. Table 1_Fig. 1

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10. Table 1_Fig. 2

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11. Table 1_Fig. 3

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12. Table 1_Fig. 4

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13. Table 1_Fig. 5

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14. Table 1_Fig. 6

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15. Scheme 3. Assumed mechanisms of activation and deactivation of palladium pyridine carboxylate complexes

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16. Scheme 4. Suggested mechanism of alcohol oxidation on pyridine carboxylate catalysts

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17. Fig. 6. Possible route of methanol oxidation in the coordination sphere of complex E according to PBE/L11 calculations

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18. Fig. 7. Experimental and theoretical time dependences of benzaldehyde concentration in the presence of Pd(OAc)2/py, T = 80°C, p(O2) = 1 atm.

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