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Review
. 2025 Jul 3;10(27):28691-28708.
doi: 10.1021/acsomega.5c03157. eCollection 2025 Jul 15.

Oxidation Reactions Promoted or Catalyzed by Organotellurium Compounds

Philipe Raphael O Campos  1 , Guilherme P P P Silva  1 , Yuga Shibuya  2 , Shinichi Koguchi  2 , Eduardo E Alberto  1
Affiliations
Review

Oxidation Reactions Promoted or Catalyzed by Organotellurium Compounds

Philipe Raphael O Campos et al. ACS Omega. .

Abstract

Oxidation of organic substrates is a pivotal transformation, with profound chemical and biological implications. This review covers the synthetic application of organotellurium compounds as promoters or activators of oxidizing agents in such reactions. This research field has evolved from utilizing stoichiometric amounts of organotellurium as oxidizing agents, producing copious amounts of side products, to using this class of compounds as catalysts. Another unique feature associated with using organotellurium compounds as catalysts for oxidation is the possibility of employing less hazardous oxidizing agents, such as peroxides or combinations of oxygen, photosensitizers, and light. These characteristics render the application of organotellurium compounds attractive from both an economic and environmental perspective.

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Figures

1
1. (a) Selenoxide syn Elimination Reaction. (b) Reduction of Peroxides Promoted by the Selenoenzyme Glutathione Peroxidase (GPx)
2
2. First Observation of an Organotellurium Compound Acting as an Oxidizing Agent
3
3. Substrates that are Commonly Used for Assessing the Oxidative Potential of Organotellurium Compounds
4
4. (a) Oxidation Reactions Using Telluroxide 18. (b) Oxidation of l-Cysteine 20, under Aqueous Conditions Using Telluroxide 18
5
5. Oxidation of Benzylic Alcohols 23 Using Tellurone 22
1
1
Polymer-tethered selenoxide 25 or telluroxide 26 was used for oxidation reactions.
6
6. (a) Oxidation of Thioamides 27 Using 26. (b) Formation of Nitriles 29 under Basic Conditions. (c) Formation of the Dimer 1,2,4-thiadiazole 28 under Acidic Conditions
2
2
Tellurinic acid anhydrides 32a–c were studied as oxidizing agents.
7
7. Evaluation of the Capacity of Tellurinic Anhydride and Telluroxide to Oxidize Organotellurium Compounds
3
3
Tellurium­(IV) derivatives 34 and 35 were employed as oxidizing agents.
8
8. Oxidation of Styrene 37 to the Corresponding Diacetate 38 Using Tellurinic Acid Anhydride 32d
9
9. Formation of Tellurenic Acid 39, the Active Species on Oxidation with Tellurinic Acid Anhydride 32d and PhTeTePh 36
10
10. (a) Preparation of Tellurenil Acetates 41 from Tellurinic Acid Anhydrides 32 and Acetic Acid. (b) Conversion of Unsaturated Alcohols 42 to Functionalized Cyclic Ether 44
11
11. Aminotelluration of Alkenes to Produce 2-Oxazolidines 47
4
4
Tellurinic acid mixed anhydrides 48a–c were used as oxidizing agents.
12
12. Conversion of Tellurides to Telluroxides Promoted by Oxygen, Light, and Photosensitizer
13
13. (a) Oxidation of Alcohols to Aldehydes or Ketones by Telluroxides 49a–b. (b) Proposed Reaction Mechanism
14
14. Oxidation of Alcohols to Aldehydes or Ketones by Tellurone 51
15
15. (a) Proposed Mechanism for the Formation of Diaryltellurium Dicarboxylates 52. (b) Utilization of Diaryltellurium Dicarboxylates 52 for the Oxidation of Benzoin Derivatives 53
16
16. First Example of an Oxidation Reaction Using a Catalytic Amount of Organotellurium
17
17. Tellurinic Anhydride 32a as a Catalyst for the Hydration of Terminal Alkynes 59
18
18. Synthesis of Bis­(p-methoxyphenyl)­tellurium Dicarboxylates 61 or 62 under Electrolysis Conditions
19
19. Polymer-Tethered Tellurinic 63 as a Catalyst for Epoxidations Using H2O2
20
20. Oxidation of Styrene 37 with t-BuOOH and 10 mol % of Ditelluride 36
21
21. (a) Conversion of Tellurapyrylium Dye 66 to the Corresponding Dihydroxytellurane 67 with H2O2. (b) Oxidation of Dyes Promoted by 66
22
22. Organotellurium as Catalytic Activators of H2O2 for the Oxidation of Halide Salts and Subsequent Halogenation of Organic Substrates
23
23. Bromination of Cyclohexene Using Tellurides, NaBr, and H2O2
5
5
Structures of organotellurium catalysts employed for the activation of H2O2.
24
24. Synthesis of Halolactones 79 and Aryl Halides 81 by Oxidation of Halide Salts with H2O2 Catalyzed by Telluride 76
25
25. Preparation of Tellurides Anchored into Solid Support
26
26. Proposed Reaction Mechanism for the Activation of H2O2 by Tellurides 8 in the Oxidation of Halide Salts
6
6
Structures of diaryl ditellurides studied as catalytic activators of H2O2.
27
27. Observed Products of Ditelluride 89b Oxidation with H2O2
28
28. Proposed Reaction Mechanism for H2O2 Activation by Ditelluride 89b in the Oxidation of Halide Salts
29
29. Attempt to Produce 1,2-dibromocyclohexene 71 Utilizing PhTeTePh 36 as a Catalyst Combined with NaBr and H2O2 in Aqueous Media
30
30. Utilization of an Immobilized Ditelluride 97 as a Catalyst for the Oxidation of Halide Salts or Thiols with H2O2
31
31. Dimerization of Thiols 12 and Polythiols 99 Using Immobilized Telluride 98 and Peroxide
32
32. Diaryltellurium Dicarboxylates 52 as Catalysts for Epoxidations with Peroxide
33
33. (a) In Situ Formation of the Active Oxidizing Agent, Pertellurinic Acid 94b. (b) Proposed Mechanism for the Epoxidation of Alkenes with Diaryltellurium Dicarboxylates 52 and Peroxide
34
34. First Reported Oxidation Reaction Using Oxygen Activated by Tellurium
35
35. First Observation of Photooxidation of Organotellurium Compounds with Oxygen
36
36. Aerobic Oxidation of Thiols 12 Using 1.0 mol % of Tellurorhodamine Dye 106
37
37. Chalcogenorhodamines 106 or 107a–c in the Photocatalytic Oxidation of Tetrahydroisoquinolines 108 under Different Reaction Conditions
38
38. Effect of Electron-Donating Groups on the Photooxidation Efficiency of Tellurorhodamine Dyes
39
39. (a) Aerobic Photooxidation of Triphenyl Phosphite 115 Using 1.0 mol % of Telluride 117. (b) Proposed Mechanism
40
40. Aerobic Photooxidation of Silanes 113 or Thiols 12 Using Organotellurium Catalysts
41
41. Aerobic Oxidation of Diaryl Tellurides
42
42. Use of an Ionic Liquid-Supported Telluride 122 for Aerobic Photooxidation of Organic Substrates
43
43. Photo-Oxidative Formation of Disulfide Bonds in Polymers Catalyzed by PhTePh
44
44. Observed Products of Telluride 8 Aerobic Photooxidation
45
45. Aerobic Oxidation of Oximes 130 Utilizing PhTeTePh 36 as a Catalyst
46
46. Proposed Mechanism for the Aerobic Oxidation of Oximes 130 Utilizing PhTeTePh 36 as a Catalyst
47
47. Cross-Dehydrogenative Phenothiazination of Phenols 137 with Phenothiazine Derivatives 138 under Aerobic Conditions Catalyzed by Telluride 136a
48
48. Proposed Mechanism for the Cross-Dehydrogenative Phenothiazination of Phenols 137 with Phenothiazine Derivatives 138 under Aerobic Conditions Catalyzed by Telluride 136a
49
49. Cross-Dehydrogenative Coupling of Anilines 143 with Phenothiazine, Ag2O, and Telluride 136a
50
50. Aerobic Dimerization of Indols 145 Promoted by Tellurides 147a–c
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