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

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Abstract

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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About the authors

O. N. Shishilov

MIREA – Russian Technological University

Author for correspondence.
Email: oshishilov@gmail.com
Russian Federation, Moscow

V. A. Polyakova

MIREA – Russian Technological University

Email: oshishilov@gmail.com
Russian Federation, Moscow

N. S. Akhmadullina

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

Email: oshishilov@gmail.com
Russian Federation, Moscow

R. S. Shamsiev

MIREA – Russian Technological University

Email: oshishilov@gmail.com
Russian Federation, Moscow

V. R. Flid

MIREA – Russian Technological University

Email: oshishilov@gmail.com
Russian Federation, Moscow

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Supplementary files

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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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