State-of-Art Advances on Silylation-Initiated Annulation Reactions

doi:10.6023/cjoc202307025

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (10): 3414-3453.DOI: 10.6023/cjoc202307025 Previous Articles Next Articles

Special Issue: 有机硅化学专辑-2023

基于硅烷化启动的环化反应研究进展

南宁^a^,^b, 吴双^a^,^b, 秦景灏^a^,^b^,^*(), 李金恒^a^,^b^,^c^,^d^,^*()

a 青岛科技大学化工学院生态化工国家重点实验室基地山东青岛 266042
b 南昌航空大学江西省持久性污染物控制与资源循环利用重点实验室南昌 330063
c 兰州大学应用有机化学国家重点实验室兰州 730000
d 河南师范大学化学化工学院河南新乡 453007

收稿日期:2023-07-27 修回日期:2023-09-09 发布日期:2023-09-15
基金资助:
国家自然科学基金(22271245); 国家自然科学基金(21964013); 河南师范大学化学化工学院开放研究基金(2021ZD01); 江西省自然科学基金(20224BAB213014); 江西省自然科学基金(20212BAB213025)

State-of-Art Advances on Silylation-Initiated Annulation Reactions

Ning Nan^a^,^b, Shuang Wu^a^,^b, Jinghao Qin^a^,^b(), Jinheng Li^a^,^b^,^c^,^d()

a State Key Laboratory Base of Eco-Chemical Engineering, College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao, Shandong 266042
b Key Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources Recycle, Nanchang Hangkong University, Nanchang 330063
c State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000
d School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007

Received:2023-07-27 Revised:2023-09-09 Published:2023-09-15
Contact: *E-mail: qjhqin@hnu.edu.cn; jhli@hnu.edu.cn
Supported by:
National Natural Science Foundation of China(22271245); National Natural Science Foundation of China(21964013); Open Research Fund of School of Chemistry and Chemical Engineering, Henan Normal University(2021ZD01); Jiangxi Provincial Natural Science Foundation(20224BAB213014); Jiangxi Provincial Natural Science Foundation(20212BAB213025)

Organosilicon compounds are important monomers and useful organic molecules in many materials, and are widely used synthetic intermediates in chemical synthesis. Therefore, people have been working hard to develop new methods to construct silicon containing chemical bond, especially C—Si bonds. Since Sakurai and Imai reported the first palladium catalyzed cycloaddition reaction of silcyclobutane with acetylene in 1975, transition metal catalyzed silyl annulation has been developed rapidly. With the rapid development of free radical reactions, researchers have expanded them to the annulation reaction between organic silicon molecules, ushering in new developments in the annulation reaction of silicon. The transition metal catalyzed silylative annualtion reaction, free radical initiated silylative annualtion reaction, and C^＋ ion initiated silylative annualtion reaction are mainly discussed. Finally, a summary of the current research progress is described.

Key words: C—H functionalization, organic silanes, unsaturated bonds, annulation reaction

Cite this article

Ning Nan, Shuang Wu, Jinghao Qin, Jinheng Li. State-of-Art Advances on Silylation-Initiated Annulation Reactions[J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3414-3453.

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Fig. & Tab. 53

Figure 1. Representative silicone ring compounds in agricultural chemicals, odorants, pharmaceuticals, advanced materials, and industrial chemicals

Scheme 1. Synergistic catalysis of Pd and Cu in the dicarbonylative benzoannulation

Scheme 2. Mechanism of dicarbonylative benzoannulation reaction catalyzed by Pd and Cu synergy

Scheme 3. Palladium/copper catalyzed methylsilylative [5＋1] benzoannulation of 3-acetoxy-1,4-enes

Scheme 4. Mechanism of palladium/copper catalyzed methylsilylative [5＋1] benzoannulation of 3-acetoxy 1,4-enes

Scheme 5. Palladium catalyzed strain release silicon-based cross coupling cyclization reaction

Scheme 6. Palladium catalyzed strain release silicon based cross coupling cyclization reaction mechanism

Scheme 7. Palladium catalyzed annulation reaction of cyclopropenes with benzylsilane cyclobutanes

Scheme 8. Mechanism of palladium catalyzed annulation of cyclopropenes with benzosilane cyclobutanes

Scheme 9. Palladium catalyzed silane annulation reaction of (hetero) aromatic hydrocarbons with tetrasilane

Scheme 10. Mechanism of palladium catalyzed silane annulation reaction between heteroaromatic hydrocarbons and tetrasilane

Scheme 11. Palladium catalyzed annulation of 2-iodoaromatic (4＋4) to octamembered silicon rings

Scheme 12. Palladium catalyzed cyclization mechanism of 2-iodoaromatic [4＋4] to octamembered silicon rings

Scheme 13. Palladium catalyzed asymmetric silylation reaction

Scheme 14. Palladium catalyzed asymmetric silylation reaction

Scheme 15. Me3SiSiMe2(On Bu) silane reagent used for rearrangement reaction to synthesize different silane rings

Scheme 16. Me3SiSiMe2(On Bu) silane reagent used for rearrangement reaction to synthesize different silane rings

Scheme 17. Palladium catalyzed intermolecular silyl C(sp2)—C(sp3) cross coupling silylative annulation reaction

Scheme 18. Palladium catalyzed asymmetric methylsilylation of difluorocyclopropenes

Scheme 19. Time controlled palladium catalyzed cascade C—H silylative annulation to synthesize silane ring reaction

Scheme 20. Mechanism of palladium catalyzed cascade C—H silylative annulation to synthesize silane rings

Scheme 21. Rhodium catalyzed annulation of 2-arylphenol derived hexagonal silicons

Scheme 22. Rhodium catalyzed annulation reaction of silicocyclobutane (SCB) with unactivated alkynes

Scheme 23. Mechanism of rhodium catalyzed cyclization reaction of silicocyclobutane (SCB) with unactivated alkynes

Scheme 24. Selective hydrosilylation of silicone alkynes catalyzed by rhodium

Scheme 25. Rhodium catalyzed spiro isomerization reaction of succinimides and pyrazolone functionalized 1,6-dienes

Scheme 26. Rh/Cu catalyzed [4＋2] annulation reaction of asymmetric alkynyl esters with silylcyclobutanes

Scheme 27. Mechanism of Rh/Cu catalyzed asymmetric alkynyl esters and silocyclobutane [4＋2] annulation reaction

Scheme 28. Asymmetric hydrosilylation catalyzed by rhodium

Scheme 29. Asymmetric ring expanding reaction of 4/5-spirosilicofluorenes with terminal alkynes catalyzed by rhodium

Scheme 30. Platinum catalyzed silylation reaction of 2-(phenylethynyl) phenylmethanols

Scheme 31. Mechanism of platinum catalyzed silicone based annulation of 2-(phenylethyl) phenylmethanols

Scheme 32. Cobalt asymmetric catalysis of hydrosilylation/cyclization of 1,6-alkynes

Scheme 33. Mechanism of Cobalt asymmetric catalysis of hydrosilylation/cyclization of 1,6-alkynes

Scheme 34. Copper catalyzed silanization cyclization reaction of 2,2'-stilbene diaryl derivatives

Scheme 35. Mechanism of copper catalyzed silanization cyclization reaction of 2,2'-stilbene diaryl derivatives

Scheme 36. Visible light catalyzed free radical cyclization reaction of silyl iodines and phenylalkynes

Scheme 37. Mechanism of visible light catalyzed free radical cyclization reaction between silyl iodide and phenylalkynes

Scheme 38. Iron catalyzed spirocyclization of N-aryl propionamides with silanes

Scheme 39. Mechanism of iron catalyzed spirocyclication of N-aryl propionamides with silanes

Scheme 40. Mn-catalyzed intermolecular oxidation radical heteroannulation reaction of N-(2-cyano)acrylamides and tert-silanes

Scheme 41. Mechanism of intermolecular oxidation radical heteroannulation reaction between N-(2-cyano) acrylamide and tert- silane catalyzed by Mn

Scheme 42. Cu catalyzed intermolecular annulation cascade reaction of oxidation free radical functionalization of Si—H and silyl C(sp3)—H bonds

Scheme 43. Mechanism of intermolecular annulation cascade reaction of Cu catalyzed Si—H and methylsilyl C(sp3)—H bonds for oxidative free radical functionalization

Scheme 44. Photocatalytic cyclization reaction of 1,6-enynes and hydrogenated silanes with Eosin Y

Scheme 45. Mechanism of cyclization reaction between 1,6-enynes and hydrogenated silanes catalyzed by Eosin Y

Scheme 46. Radical addition translocation cyclization reaction initiated by methylsilyl radical

Scheme 47. Triphenylmethyl cation initiated annulation reaction of benzyl substituted vinyl cyclopropanes with hydrogenated silanes

Scheme 48. Mechanism of annulation reaction between benzyl substituted vinyl cyclopropanes and hydrogenated silanes initiated by triphenylmethyl cation

Scheme 49. Hydrogenation silanization of aryl substituted allenes initiated by triphenylmethyl cations and promoted by methylsilyl ions

Scheme 50. Mechanism ofhydrosilylation reaction of aryl substituted allenes initiated by triphenylmethyl cations and promoted by methylsilyl ions

Scheme 51. Nazarov annulation reaction of cross conjugated polyenes with methylsilyl ions

Scheme 52. Nazarov annulation reaction mechanism of cross conjugated polyenes with methylsilyl ions

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基于硅烷化启动的环化反应研究进展

State-of-Art Advances on Silylation-Initiated Annulation Reactions

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