C(sp3)—H键直接催化硅基化反应研究进展

doi:10.6023/cjoc202109017

摘要/Abstract

含C(sp³)—Si键的有机硅化合物在材料科学、药物化学和精细化学品合成等研究领域有着广泛的应用. 通过C(sp³)—H的直接催化硅基化形成C(sp³)—Si键具有高的原子经济性和步骤经济性特点, 近些年已成为含C(sp³)—Si键的新型有机硅分子合成领域的一个研究热点. 详细总结了C(sp³)—H键直接催化硅基化反应的研究进展, 并探讨了相关反应的机理和应用范围.

关键词: 过渡金属, C(sp³)—H硅基化, C(sp³)—Si键, 有机硅, 非过渡金属

Organosilicon compounds containing C(sp³)—Si bonds are widely used in many research fields, such as material science, pharmaceutical chemistry and fine chemical synthesis. In recent years, due to its high atomic economy and step economy properties, the direct catalytic silylation of C(sp³)—H bonds to form C(sp³)—Si bonds has become one of the research hotspots in the syntheis of new organosilicones containing C(sp³)—Si bonds. The research progress of direct catalytic silylation of C(sp³)—H bonds is summarized in detail, and the mechanism and application range of related silylation reactions are also discussed.

Key words: transition-metal, C(sp³)—H silylation, C(sp³)—Si bond, organosilicone, non-transition metal

引用此文

程异, 胡荣静, 陈晓琪, 杨浩, 牛晓康, 杨磊. C(sp³)—H键直接催化硅基化反应研究进展[J]. 有机化学, 2022, 42(2): 323-343.

Yi Cheng, Rongjing Hu, Xiaoqi Chen, Hao Yang, Xiaokang Niu, Lei Yang. Recent Progress in Direct Catalytic C(sp³)—H Silylation Reactions[J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 323-343.

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图/表 56

图1. 具有生物活性的含C(sp3)—Si键的有机硅化合物示例

Figure 1. Examples of C(sp3)—Si-containing organicsilicon compounds of biological active properties

图2. C(sp3)—H键直接催化硅基化反应总览

Figure 2. Overall view of direct catalytic silylation reactions of C(sp3)—H bonds

图式1. 铱催化醇或酮中γ-C(sp3)—H硅基化反应

Scheme 1. Ir-catalyzed γ-C(sp3)—H silylation of alcohols and ketones

图式2. 铱催化氮原子导向的甲基C(sp3)—H硅烷基化反应

Scheme 2. Ir-catalyzed nitrogen-directed methyl C(sp3)—H silylation

图式3. 一锅法合成全保护的L-甘露糖苷

Scheme 3. One-pot sequence for the synthesis of fully protected L-mannoside

图式4. 铱催化二级C(sp3)—H硅基化合成1,3-二醇

Scheme 4. Ir-catalyzed silylation of secondary C(sp3)—H bonds for the synthesis of 1,3-diols

图式5. 1-烯烃合成1,4-二醇衍生物

Scheme 5. Synthesis of 1,4-diols from 1-alkenes

图式6. 铱催化二级胺导向的分子内苄位C(sp3)—H硅基化

Scheme 6. Ir-catalyzed intramolecular silylation of benzylic C(sp3)—H bonds directed by a secondary amine

图式7. 铱和铁通过烷烃脱氢和异构化-硅氢加成催化各种烷烃的硅基化

Scheme 7. Iridium-iron-catalyzed silylation of various alkanes via alkane dehydrogenation and isomerization-hydrosilylation

图式8. 铱催化2-和4-烷基吡啶苄位C(sp3)—H硅基化

Scheme 8. Ir-catalyzed benzylic C(sp3)—H silylation of 2- alkylpyridines and 4-alkylpyridines

图式9. 铱催化2-烷基吡啶硅基化反应可能机理

Scheme 9. Proposed reaction mechanism for Ir-catalyzed benzylic C(sp3)—H silylation of 2-alkylpyridines

图式10. 阳离子铱催化2-烷基-1,3-唑苄位C(sp3)—H硅基化

Scheme 10. Cationic iridium-catalyzed benzylic C(sp3)—H silylation of 2-alkyl-1,3-azoles

图式11. 铱催化分子内对映选择性甲基C(sp3)—H硅基化

Scheme 11. Ir-catalyzed enantioselective, intramolecular silylation of methyl C—H bonds

图式12. 形式上的醇β-C(sp3)—H羟基化

Scheme 12. Formal β-C(sp3)—H hydroxylation of alcohols

图式13. 铱催化脂肪胺分子内C(sp3)—H硅烷基化

Scheme 13. Ir-catalyzed intramolecular C(sp3)—H silylation of aliphatic amines

图式14. 铱催化杂环芳烃甲基C(sp3)—H硅烷基化

Scheme 14. Ir-catalyzed methyl C(sp3)—H silylation of heteroarenes

图式15. 钌催化C(sp3)—H硅基化和氟化物促进的羧基化

Scheme 15. Ru-catalyzed C(sp3)—H silylation and fluoride- mediated carboxylation

图式16. 钌催化未活化C(sp3)—H键的硅烷基化

Scheme 16. Ru-catalyzed silylation of unreactive C(sp3)—H bonds

图式17. 钌催化分子内C(sp3)—H硅烷化反应

Scheme 17. Ru-catalyzed intramolecular silylation of C(sp3)—H bonds

图式18. 钌催化芳基膦中C(sp3)—H硅烷基化

Scheme 18. Ru-catalyzed silylation of C(sp3)—H bonds in arylphosphines

图式19. 铑催化甲苯C(sp3)—H硅烷基化

Scheme 19. Rh-catalyzed C(sp3)—H silylation of toluene

图式20. 铑催化分子内C(sp3)—H硅基化

Scheme 20. Rh-catalyzed intramolecular C(sp3)—H silylation

图式21. 铑催化分子内C(sp3)—H硅基化反应机理

Scheme 21. Proposed reaction mechanism for Rh-catalyzed intramolecular C(sp3)—H silylation

图式22. 铑催化分子内C(sp3)—H硅烷基化反应

Scheme 22. Rh-catalyzed intramolecular C(sp3)—H silylation

图式23. 芳香酯、酮和醛的还原苄基C(sp3)—H硅烷基化

Scheme 23. Sequential reductive benzylic C(sp3)—H silylation of aromatic ester, ketone and aldehyde

图式24. 铑催化分子内环丙基C(sp3)—H硅烷基化

Scheme 24. Rh-catalyzed intramolecular silylation of cyclopropyl C(sp3)—H bonds

图式25. 铑催化叔醇C(sp3)—H硅烷基化反应

Scheme 25. Rh-catalyzed C(sp3)—H silylation of tertiary alcohols

图式26. 对映选择性C(sp3)—H硅基化/烯烃氢硅烷化

Scheme 26. Enantioselective silylation of aliphatic C—H bonds/alkene hydrosilylation

图式27. 铑催化去对称化和动力学拆分C(sp3)—H硅基化

Scheme 27. Rh-catalyzed enantioselective C(sp3)—H silylation via desymmetrization and kinetic resolution

图式28. 钯催化烯丙基C—H氧化硅基化

Scheme 28. Pd-catalyzed oxidative allylic C—H silylation

图式29. 钯催化羧酸酰胺的C(sp3)—H硅烷基化

Scheme 29. Pd-catalyzed C(sp3)—H silylation of carboxamides with hexamethyldisilane

图式30. 钯催化酰胺导向C(sp3)—H硅烷基化

Scheme 30. Pd-catalyzed amide-oriented C(sp3)—H silylation

图式31. 钯催化甲基和亚甲基C(sp3)—H硅烷基化

Scheme 31. Pd-catalyzed silylation of primary and secondary C(sp3)—H bonds

图式32. 钯催化酰胺C(sp3)—H硅烷基化

Scheme 32. Pd-catalyzed C(sp3)—H silylation of carboxamides

图式33. 钯催化酰胺C(sp3)—H硅烷基化反应机理

Scheme 33. Proposed mechanism of Pd-catalyzed C(sp3)—H silylation of carboxamides

图式34. 钯催化酰胺类C(sp3)—H硅烷基化反应

Scheme 34. Pd-catalyzed C(sp3)—H silylation reactions of carboxamides

图式35. 钯催化1-叔丁基-2-溴苯衍生物双硅烷基化

Scheme 35. Pd-catalyzed disilylation of 1-(tert-butyl)-2-bromobenzene derivatives

图式36. 钯催化α-氨基酸和多肽γ-C(sp3)—H硅基化

Scheme 36. Pd-catalyzed γ-C(sp3)—H silylation of α-amino acids and peptides

图式37. 钯催化酮中C(sp3)—H硅基化反应

Scheme 37. Pd-catalyzed C(sp3)—H silylation of ketones

图式38. 镍催化对二甲苯和均三甲苯C(sp3)—H硅烷基化反应

Scheme 38. Ni-catalyzed C(sp3)—H silylation of p-xylene and mesitylene

图式39. 碱催化芳烃苄位C(sp3)—H硅基化

Scheme 39. Base-catalyzed silylation of benzylic C(sp3)—H bonds of arenes

图式40. 钙催化2-甲基苯甲醚C(sp3)—H硅烷基化反应机理

Scheme 40. Proposed mechanism of Ca-catalyzed C(sp3)—H silylation of 2-methylanisol

图式41. B(C6F5)3催化三级胺C(sp3)—H硅基化

Scheme 41. B(C6F5)3-catalyzed C(sp3)—H silylation of tertiary amines

图式42. B(C6F5)3催化非环状叔胺两次C(sp3)—H硅基化 B(C6F5)3催化非环状叔胺两次C(sp3)—H硅基化

Scheme 42. B(C6F5)3-catalyzed two-fold C(sp3)—H silylation of acyclic tertiary amines B(C6F5)3-catalyzed two-fold C(sp3)—H silylation of acyclic tertiary amines

图式43. 钌催化甲基硼酸α-C(sp3)—H硅基化反应

Scheme 43. Ru-catalyzed α-C(sp3)—H silylation of methylboronic acid

图式44. 铑催化氮原子邻位C(sp3)—H硅烷基化反应

Scheme 44. Rh-catalyzed silylation of C(sp3)—H bonds adjacent to a nitrogen atom

图式45. 通过[1,5]-氢转移介导的脂肪C—H硅烷基化

Scheme 45. Silylation of aliphatic C—H bonds mediated by [1,5]-hydrogen transfer

图式46. 铜催化酰胺氮原子邻位C(sp3)—H硅基化

Scheme 46. Cu-catalyzed silylation of C(sp3)—H bonds adjacent to amide nitrogen atom

图式47. 钌催化酰胺和脲中C(sp3)—H硅基化

Scheme 47. Ru-catalyzed C(sp3)—H bond silylation of amides and carbamides

图式48. 钌催化氮原子α-C(sp3)—H分子内硅基化

Scheme 48. Ru-catalyzed intramolecular silylation of C(sp3)—H bonds α to N-atom

图式49. 钌催化分子内氧原子α-C(sp3)—H硅基化

Scheme 49. Ru-catalyzed intramolecular silylation of α to O-atom

图式50. 钇催化烷基和芳基甲硫醚C(sp3)—H硅基化

Scheme 50. Y-catalyzed methyl C(sp3)—H silylation of alkyl and aryl methyl sulfide

图式51. 钌或铑催化硅烷脱氢偶联反应

Scheme 51. Ru or Rh-catalyzed dehydrogenative coupling of silanes

图式52. 铱催化苄基甲基硅烷的脱氢二聚反应

Scheme 52. Ir-catalyzed dehydrogenative dimerization of benzylmethylsilanes

图式53. 钌催化硅或锗α-位甲基C(sp3)—H硅基化反应

Scheme 53. Ru-catalyzed silylation of methyl C(sp3)—H bonds of α to Si-atom or Ge-atom

图式54. 钪催化甲烷C(sp3)—H硅基化

Scheme 54. Sc-catalyzed C(sp3)—H silylation of methane

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C(sp³)—H键直接催化硅基化反应研究进展

Recent Progress in Direct Catalytic C(sp³)—H Silylation Reactions

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