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

doi:10.6023/cjoc202109017

Abstract

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

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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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Fig. & Tab. 56

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Scheme 52. Ir-catalyzed dehydrogenative dimerization of benzylmethylsilanes

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

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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[6]	Rui Wang, Lang Gao, Cen Zhou, Xiao Zhang. Haloperfluoroalkylation of Unactivated Terminal Alkenes over Phenylphenothiazine-Based Porous Organic Polymers [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1136-1145.
[7]	Sining Qin. Research Progress in C—S Coupling Reactions of Aryl Halides [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3761-3783.
[8]	Yan Zeng, Fei Ye. Research Progress on New Catalytic Reaction Systems for Asymmetric Synthesis of Silicon-Stereogenic Center Containing Compounds [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3388-3413.
[9]	Qiyang Li, Haiyan Zhang, Wenbo Liu. Research Progress in Transition-Metal-Free C—Si Bond Formation [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3470-3490.
[10]	Cheng Yuan, Changduo Pan. Recent Advances in the N-Aryl C—H Functionalization Using 7-Azaindole as Intrinsic Directing Group [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 156-170.
[11]	Jinyu Zhang, Tianfen Liu, Le Wang, Xiaoming Wang. Recent Process in the in situ Generated Metal Nanocluster Catalysis [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2331-2341.
[12]	Cheng Gong, Jian Tang, Fei Xu, Pengjie Li, Zetian Wang, Yumin Zhang, Guoxian Yu, Liang Wang. Recent Advances in Transition-Metal-Catalyzed C—H Activation of Pyridone/Isoquinolones [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 1925-1949.
[13]	Yazhou Wang, Yuhang Zhu, Lixia Xu, Rui He, Jian Zhang. Recent Advances in Geminal-Group-Directed Alkenyl C—H Functionalization [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2000-2014.
[14]	Siqi Cong, Mengya Liu, Siyuan Peng, Qiucui Zheng, Mengjiao Li, Yan Guo, Feixian Luo. Cross-Coupling of C—Si Bond by Using of Silyl Electrophiles [J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 384-390.
[15]	Yaohui Xu, Zhen Wu, Xinxin Wu, Chen Zhu. Transition-Metal Free Radical-Mediated C—H Bond Alkynylation and Allylation of Ethers, Aldehydes and Amides [J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 4340-4349.

C(sp3)—H键直接催化硅基化反应研究进展