亚砜叶立德在C—H键活化反应中的应用研究进展

doi:10.6023/cjoc202007037

摘要/Abstract

过渡金属催化的导向C—H键活化反应具有反应效率高、选择性好、原子经济等优点, 特别是卡宾前体参与的 C—H活化反应已经发展为一种新颖的构筑碳碳键的合成策略. 相比于传统的重氮化合物等卡宾前体, 亚砜叶立德作为一种新型的卡宾前体, 具有易于制备、性质稳定、操作安全等诸多优点, 被广泛应用于C—H活化反应, 可以便捷地转化成各种酰甲基化或环化产物. 综述了近几年来亚砜叶立德在C—H键活化反应中的应用研究进展, 并对其今后的发展趋势进行了展望.

关键词: 过渡金属, C—H活化, 卡宾前体, 亚砜叶立德

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

引用此文

洪超, 蒋希程, 于书玲, 刘占祥, 张玉红. 亚砜叶立德在C—H键活化反应中的应用研究进展[J]. 有机化学, 2021, 41(3): 888-906.

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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图/表 64

图式1. 利用亚砜叶立德作卡宾前体的C—H官能团化反应机理

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

图式2. 三价铑催化的2-苯基吡啶与亚砜叶立德交叉偶联反应

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

图式3. 2-苯基吡啶的邻位C—H活化/环化机理

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

图式4. Rh(III)催化芳烃的C—H键酰甲基化反应

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

图式5. 铑催化2-芳基-1H苯并[d]咪唑与亚砜叶立德的环化反应

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

图式6. Rh(III)催化N-唑啉亚胺的C—H活化/环化反应

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

图式7. 三价铑催化C-烯基唑与亚砜叶立德C—H官能团化反应

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

图式8. 氨基吡唑、醛和亚砜叶立德三组分经由C—H活化的偶联反应

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

图式9. 三价铑催化2-芳基吲哚与亚砜叶立德的C—H官能团化反应

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

图式10. 三价铑催化N-苯基-吡啶-2-胺与亚砜叶立德的分子间环化反应

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

图式11. 水介导的芳烃与亚砜叶立德的C—H活化反应

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

图式12. 三价铑催化的区域选择性C(3)—H酰甲基化反应

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

图式13. 三价铑催化2-苯基噁唑啉与亚砜叶立德的环化反应

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

图式14. 三价铑催化N-芳基-7-氮杂吲哚与亚砜叶立德的C—H环化反应

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

图式15. 三价铑催化2-芳基喹唑啉-4(3H)-酮与亚砜叶立德的C—H环化反应

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

图式16. 三价铑催化6-芳基嘌呤与亚砜叶立德的C—H酰甲基化反应

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

图式17. Rh(III)催化芳烃与亚砜叶立德的偶联环化反应

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

图式18. 苯甲酰亚胺酸乙酯与亚砜叶立德的双邻位C—H官能团化和双环化反应

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

图式19. 苯甲酰亚胺酸乙酯与亚砜叶立德的双C—H官能团化和双环化反应机理

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

图式20. 添加剂控制的N-芳基脒与亚砜叶立德的选择性C—H活化/环化反应

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

图式21. Rh(III)催化N-甲氧基苯甲酰胺的邻位C—H活化/环化反应

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

图式22. 三价铑催化偶氮苯与亚砜叶立德的[4+1]环化反应

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

图式23. 三价铑催化芳肼与亚砜叶立德的环化反应

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

图式24. 三价铑催化N-亚硝基苯胺与亚砜叶立德的环化反应

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

图式25. 三价铑催化N-亚硝基苯胺与亚砜叶立德的酰甲基化/环化反应

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

图式26. 三价铑催化喹啉-N-氧化物与亚砜叶立德的C(8)—H酰甲基化反应

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

图式27. 三价铑催化烯胺酮与亚砜叶立德的C—H活化/环化反应

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

图式28. 三价铑催化的醛基C—H官能团化反应

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

图式29. 三价铑催化水杨醛与亚砜叶立德的C—H活化/环化反应

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

图式30. Rh(III)催化苯甲酰乙腈与亚砜叶立德的反应

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

图式31. Rh(III)催化N-(氰基乙酰基)二氢吲哚与亚砜叶立德的C—H活化反应

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

图式32. Rh(III)催化苯甲酰乙腈与亚砜叶立德反应合成1-萘酚

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

图式33. 3-甲酰基乙腈吲哚与亚砜叶立德或重氮化合物的C—H官能团化反应

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

图式34. 二价钌催化S-苯基亚砜亚胺与亚砜叶立德的偶联-环化反应

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

图式35. 通过弱的氧配位的钌(II/IV)催化的C—H活化反应

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

图式36. 二价钌催化苯甲亚胺酸乙酯与亚砜叶立德的偶联/环化反应

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

图式37. 二价钌催化N-芳基-2-氨基吡啶与亚砜叶立德的分子间环化反应

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

图式38. 二价钌催化芳基脒与亚砜叶立德的环化反应

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

图式39. 二价钌催化的芳(杂)环的酰甲基化反应

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

图式40. 二价钌催化2-烯基苯胺与亚砜叶立德的[5+1]环化反应

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

图式41. 二价钌催化N-芳基酞嗪-1,4-二酮与亚砜叶立德的C—H酰甲基化反应

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

图式42. 二价钌催化2-吡啶酮与亚砜叶立德的C—H酰甲基化反应

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

图式43. 一价铱催化苯胺或烯胺与亚砜叶立德的环化反应

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

图式44. 三价铱催化吡唑啉酮与亚砜叶立德的C—H键活化/环化反应

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

图式45. 三价铱催化的C—H官能团化反应合成2-取代吲哚

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

图式46. 硫醚导向的吲哚C(4)位选择性碳氢键酰甲基化反应

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

图式47. 三价钴催化的芳烃的C—H酰甲基化反应

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

图式48. 二价钯催化亚砜叶立德的氧化烯丙基化反应

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

图式49. 二价铜介导的N-磺酰基苯腙与亚砜叶立德的[4+1]环加成反应

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

图式50. 三价铑催化亚砜叶立德的邻位C—H活化/环化反应

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

图式51. 三价铑催化亚砜叶立德的邻位C—H活化/环化反应机理

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

图式52. 三价铑催化亚砜叶立德与α-重氮化合物的级联反应

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

图式53. 三价铑催化亚砜叶立德与胺茴内酐的[4+1]环化反应

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

图式54. 三价铑催化氧杂/氮杂双环烯烃与亚砜叶立德的化学发散型偶联反应

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

图式55. 三价铑催化亚砜叶立德的C—H活化/环化和内酯化反应

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

图式56. 三价铑催化亚砜叶立德与累积二烯酸酯的环化偶联反应

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

图式57. 三价铑催化亚砜叶立德与烯烃的环化反应

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

图式58. 三价铑催化亚砜叶立德与丙烯酸酯的环化反应

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

图式59. 三价铑催化亚砜叶立德与苯醌的偶联环化反应

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

图式60. 三价钴催化亚砜叶立德的邻位C—H酰胺化反应

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

图式61. 三价钴催化亚砜叶立德与炔烃的C—H活化和环化反应

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

图式62. 二价钌催化的亚砜叶立德经由C—H活化/环化的自身偶联反应

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

图式63. 二价钌催化的亚砜叶立德自身偶联反应机理

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

图式64. 二价钌催化亚砜叶立德经由双重C—H/C—C活化合成异香豆素

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

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