Recent Progress on the Application of Sulfoxonium Ylides in C—H Activation

doi:10.6023/cjoc202007037

Abstract

Transition-metal-catalyzed chelation-assisted C—H functionalization has been increasingly explored as an efficient and atom-economical strategy for construction of C—C bonds. In particular, employing the carbene synthons as a coupling partner in C—H activation has been significantly developed. Compared with the traditional carbene precursors such as diazo compounds, sulfoxonium ylides are easier to synthesize and safer in reaction, which can be employed as practical alternatives in metal-carbene reactions. Recently, the coupling reactions of sulfoxonium ylides with organometallic intermediates, generated via C—H bond activation, have been reported. They have served as privileged synthetic skeletons to accessortho-C—H acylmethylated or cyclized compounds. The recent progress on the application of sulfoxonium ylides in C—H activation is summarized and the future research direction is prospect.

Key words: transition-metal, C—H activation, carbene precursor, sulfoxonium ylide

Cite this article

Chao Hong, Xicheng Jiang, Shuling Yu, Zhanxiang Liu, Yuhong Zhang. Recent Progress on the Application of Sulfoxonium Ylides in C—H Activation[J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 888-906.

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Fig. & Tab. 64

Scheme 1. Mechanism of C—H functionalization using sulfoxonium ylides as carbene precursors

Scheme 2. Rhodium(III)-catalyzed cross-coupling reaction of 2-phenylpyridines with sulfoxonium ylides

Scheme 3. Mechanism of C—H activation and cyclization of 2-phenylpyridines

Scheme 4. Rh(III)-catalyzed C—H acylmethylation of arenes

Scheme 5. Rhodium-catalyzed annulation of 2-aryl-1H-benzo- [d]imidazoles and sulfoxonium ylides

Scheme 6. Rhodium(III)-catalyzed C—H activation/annulation reaction of N-azoloimines

Scheme 7. Rhodium(III)-catalyzed C—H functionalization of C-alkenyl azoles with sulfoxonium ylides

Scheme 8. Three-component coupling of aminopyrazoles, aldehydes and sulfoxonium ylides via C—H activation

Scheme 9. Rh(III)-catalyzed C—H functionalization of 2- arylindoles with sulfoxonium ylides

Scheme 10. Rhodium(III)-catalyzed intermolecular cyclization of N-phenylpyridin-2-amines with sulfoxonium ylides

Scheme 11. Water-mediated C—H activation of arenes with sulfoxonium ylides

Scheme 12. Rhodium(III)-catalyzed regioselective C(3)—H acylmethylation reaction

Scheme 13. Rh(III)-catalyzed annulation reaction between 2- phenyl-oxazolines and sulfoxonium ylides

Scheme 14. Rh(III)-catalyzed C—H annulation reaction of N-aryl-7-azaindoles with sulfoxonium ylides

Scheme 15. Rh(III)-catalyzed C—H annulation reaction of 2-arylquinazolin-4(3H)-ones with sulfoxonium ylides

Scheme 16. Rh(III)-catalyzed C—H acylmethylation of 6-aryl- purines with sulfoxonium ylides

Scheme 17. Rhodium(III)-catalyzed annulative coupling between arenes and sulfoxonium ylides

Scheme 18. Dual ortho-C—H functionalization and dual cyclization between ethylbenzimidates and sulfoxonium ylides

Scheme 19. Mechanism of dual C—H functionalization and dual cyclization between ethylbenzimidates and sulfoxonium ylides

Scheme 20. Additive-controlled selective C—H activation/ annulation of N-arylamidines and sulfoxonium ylides

Scheme 21. Rh(III)-catalyzed C—H activation/annulation reaction of N-methoxybenzamides

Scheme 22. Rhodium(III)-catalyzed [4+1] annulation of azobenzenes with sulfoxonium ylides

Scheme 23. Rhodium(III)-catalyzed annulation of arylhydrazines with sulfoxonium ylides

Scheme 24. Rhodium(III)-catalyzed cyclization of N-nitrosoani- lines with sulfoxonium ylides

Scheme 25. Rhodium(III)-catalyzed acylmethylation/cyclization of N-nitrosoanilines with sulfoxonium ylides

Scheme 26. Rh(III)-catalyzed selective C(8)—H acylmethylation of quinoline N-oxides with sulfoxonium ylides

Scheme 27. Rhodium-catalyzed C—H activation/cyclization of enaminones with sulfoxonium ylides

Scheme 28. Rh(III)-catalyzed aldehydic C—H functionalization reaction

Scheme 29. Rh(III)-catalyzed C—H activation/annulation of salicyl aldehydes with sulfoxonium ylides

Scheme 30. Rh(III)-catalyzed reaction of benzoylacetonitriles with sulfoxonium ylides

Scheme 31. Rh(III)-catalyzed C—H activation reaction of N-cyanoacetylindolines with sulfoxonium ylides

Scheme 32. Rhodium(III)-catalyzed reaction of benzoylacetonitriles and sulfoxonium ylides to 1-naphthols

Scheme 33. C—H functionalization of 3-formylacetonitrile indoles with sulfoxonium ylides or diazo compounds

Scheme 34. Ru(II)-catalyzed coupling-cyclization of S-phenyl sulfoximines with sulfoxonium ylides

Scheme 35. Ruthenium(II/IV)-catalyzed C—H activation by weak O-coordination

Scheme 36. Ruthenium(II)-catalyzed coupling/cyclization of benzimidates and sulfoxonium ylides

Scheme 37. Ruthenium(II)-catalyzed intermolecular annulation of N-aryl-2-aminopyridines and sulfoxonium ylides

Scheme 38. Ruthenium(II)-catalyzed annulation reaction of arylamidines and sulfoxonium ylides

Scheme 39. Ruthenium(II)-catalyzed C-H acylmethylation reaction of (hetero)arenes

Scheme 40. Ruthenium(II)-catalyzed [5+1] annulation reaction of 2-alkenylanilines and sulfoxonium ylides

Scheme 41. Ruthenium(II)-catalyzed C—H acylmethylation of N-arylphthalazine-1,4-diones with sulfoxonium ylides

Scheme 42. Ruthenium(II)-catalyzed C—H acylmethylation of 2-pyridones with sulfoxonium ylides

Scheme 43. Iridium(I)-catalyzed cyclization reaction of anilines or enamines with sulfoxonium ylides

Scheme 44. Iridium(III)-catalyzed C—H activation/annulation of pyrazolones and sulfoxonium ylides

Scheme 45. Synthesis of 2-substituted indoles by iridium(III)- catalyzed C—H functionalization

Scheme 46. Thioether-directed C(4)-selective C—H acylmethylation of indoles

Scheme 47. Co(III)-catalyzed C—H acylmethylation of arenes

Scheme 48. Palladium(II)-catalyzed oxidative allylation of sulfoxonium ylides

Scheme 49. Copper(II)-mediated [4+1] cycloaddition reaction of N-sulfonylhydrazones and sulfoxonium ylides

Scheme 50. Rhodium(III)-catalyzed ortho-C—H activation/ cyclization of sulfoxonium ylides

Scheme 51. Mechanism of rhodium(III)-catalyzed ortho-C—H activation/cyclization of sulfoxonium ylides

Scheme 52. Rh(III)-catalyzed cascade reaction of sulfoxonium ylides with α-diazocarbonyl compounds

Scheme 53. Rhodium(III)-catalyzed [4+1] annulation reaction of sulfoxonium ylides and anthranils

Scheme 54. Rhodium(III)-catalyzed chemo-divergent coupling of oxa/azabicyclic ole?ns with sulfoxonium ylides

Scheme 55. Rh(III)-catalyzed C—H activation/annulation and lactonization of sulfoxonium ylides

Scheme 56. Rhodium(III)-catalyzed annulative coupling of sulfoxonium ylides and allenoates

Scheme 57. Rh(III)-catalyzed annulation reaction of sulfoxonium ylides and alkenes

Scheme 58. Rhodium(III)-catalyzed annulation of sulfoxonium ylides with acrylates

Scheme 59. Rhodium(III)-catalyzed coupling and annulation of sulfoxonium ylides with quinones

Scheme 60. Cobalt(III)-catalyzed ortho-C—H amidation of sulfoxonium ylides

Scheme 61. Co(III)-catalyzed C—H activation and cyclization of sulfoxonium ylides with alkynes

Scheme 62. Ruthenium(II)-catalyzed homocoupling of sulfoxonium ylides via C—H activation/annulation

Scheme 63. Proposed reaction mechanism of ruthenium(II)- catalyzed homocoupling of sulfoxonium ylides

Scheme 64. Ruthenium(II)-catalyzed synthesis of isocoumarins via dual C—H/C—C activation of sulfoxonium ylides

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