Transition Metal-Free C—H Thiocyanation and Selenocyanation Based on Thermochemical, Photocatalytic and Electrochemical Process

doi:10.6023/cjoc202212035

Abstract

Thiocyano and selenocyano are both important functional groups with broad application in organic synthesis. Such functional structures also occur frequently in molecules possessing valuable biological and pharmaceutical activities, optical functions, and catalytic profiles. Therefore, developing synthetic methods toward diverse organo thio-/selenocyanates as well as the tandem annulation for the construction of diverse heterocyclic scaffolds keep receiving high interests. The advances on the synthesis of organo thio-/selenocyanates via transition metal-free C—H thiocyanation or selenocyanation as well as the tandem annulation reactions based on such C—H functionalization are reviewed.

Key words: transition metal-free, C—H bond, thiocyanation, selenocyanation, thermochemistry, photocatalysis

Cite this article

Zhongrong Xu, Jieping Wan, Yunyun Liu. Transition Metal-Free C—H Thiocyanation and Selenocyanation Based on Thermochemical, Photocatalytic and Electrochemical Process[J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2425-2446.

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Fig. & Tab. 57

Figure 1. Selected drugs and bioactive molecules containing thio-/selenocyanate groups

Scheme 1. Electrochemical C—H thiocyanation indoles and analogous heterocycles

Scheme 2. Thiocyanation of electron rich arenes with the promotion of TCAA

Scheme 3. Electrochemical thiocyanation/selenocyanation of electron rich arenes

Scheme 4. NIS-catalyzed selenocyanation and thiocyanation of electron rich arenes

Scheme 5. Synthesis of 3-thiocyanatoimidazo[1,2-a]pyridines by the combination of NCS/NaSCN

Scheme 6. Thiourea/NCS/NH4SCN system for electrophilic thiocyanation of indoles and aromatic amines

Scheme 7. Regioselective thiocyanation in water using GO/ H2O2

Scheme 8. Ultrasonic promoted thiocyanation with HFIP as solvent

Scheme 9. Electrophilic thiocyanation reaction using N-thiocyanatosaccharin

Scheme 10. Direct electrophilic thiocyanation reaction using N-thiocyanatodibenzenesulfonimide

Scheme 11. Thiocyanation reaction of pyrrolo[1,2-a]quinoxa- line promoted by NCS

Scheme 12. NO2-catalyzed thiocyanation aromatics and thiophenes

Scheme 13. Regioselective synthesis of thiocyanates using K2S2O8 as oxidant

Scheme 14. Thiocyanation reaction of aromatic compounds with TMSSCN

Scheme 15. Electrochemical thiocyanation of pyrazolo[1,5-a]- pyrimidines

Scheme 16. Visible light method to promote indole C-3 thiocyanation

Scheme 17. Photocatalytic thiocyanation of indoles catalyzed by photocatalysts

Scheme 18. Photocatalytic imidazole heterocyclic thiocyanation

Scheme 19. Photocatalytic cascade C—H thiocyanation and thiazole annulation

Scheme 20. Synthesis of 2-aminobenzothiazole via aniline C—H thiocyanation

Scheme 21. Visible-light aerobic aromatic C—H thiocyanation

Scheme 22. ARS-TiO2 as photocatalyst for the photocatalytic C(sp2)—H thiocyanation

Scheme 23. Macrocycles C—H thiocyanation

Scheme 24. Thiocyanation of imidazole heterocycles

Scheme 25. Synthesis of pyrazole thiocyanate through C—H thiocyanation

Scheme 26. Synthesis of p-thiocyanoaniline using K2S2O8 as oxidant

Scheme 27. Ball milling synthesis of aryl thiocyanates

Scheme 28. Thiocyanation of imidazolopyridine in an aqueous medium

Scheme 29. Selectfluor mediated C—H thiocyanation and selenocyanation

Scheme 30. Electrochemical thiocyanation of five-membered aromatic Heterocycles

Scheme 31. Thiocyanation of o-hydroxyphenyl enaminones

Scheme 32. Thiocyanation of 4-quinolones

Scheme 33. Regioselective selenocyanation of N-aryl enaminone

Scheme 34. Regioselective synthesis of 2-iminothiazole via C—H thiocyanation

Scheme 35. Solvent-controlled synthesis of α-thiocyanoenamines and 2-aminothiazoles

Scheme 36. Thiocyanation of enaminones using PhI(OAc)2 as oxidant

Scheme 37. Thiocyanation of diverse amino and enamine derivatives

Scheme 38. Photocatalytic α-C—H thiocyanation of tertiary enaminones

Scheme 39. Photocatalytic thiocyanation of 2-aryl-quinolin-4- ones and anilines

Scheme 40. Thiocyanation reaction of 4-aminocoumarins

Scheme 41. Electrochemical thiocyanation and C—N transamination of enaminones

Scheme 42. Thiocyanation of ketene disulfides, terminal olefins and hydrazine

Scheme 43. H2O-controlled selective thiocyanation of internal olefins

Scheme 44. Selenocyanation of aromatic ketones

Scheme 45. Electrophilic selenocyanation of different C(sp3)—H and C(sp2)—H bonds

Scheme 46. Electrochemically thiocyanation of ketones

Scheme 47. Selenocyanation of ketones, β-keto esters and enamides silyl enolates

Scheme 48. Thiocyanation of pyrazolin-5-ones

Scheme 49. Paired electrochemical thiocyanation of 1,3-diketones

Scheme 50. Photocatalytic thiocyanation of ketones

Scheme 51. Organocatalytic α?thiocyanation of cyclic β?keto- esters

Scheme 52. Organocatalytic asymmetric α?thiocyanation of oxindoles

Scheme 53. Visible-light-induced α-C(sp3)—H thiocyanation of tertiary amines

Scheme 54. AIBN-initiated direct thiocyanation of benzylic C—H bond

Scheme 55. Electrochemical thiocyanation of benzylic C—H bonds

Scheme 56. Photo-induced benzylic C—H thiocyanates

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