基于硅烷化启动的环化反应研究进展

doi:10.6023/cjoc202307025

有机化学 ›› 2023, Vol. 43 ›› Issue (10): 3414-3453.DOI: 10.6023/cjoc202307025 上一篇下一篇

所属专题：有机硅化学专辑-2023

综述与进展

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)

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摘要/Abstract

有机硅化合物是许多材料的重要基元和有用的有机分子, 是化学合成中用途广泛的合成中间体. 因此, 化学家们一直致力于开发构建含硅化学键的新方法, 特别是C—Si键. 自从Sakurai和Imai在1975年报道了第一个钯催化的硅环丁烷与炔的环加成反应以来, 过渡金属催化硅基环化反应得到了迅速的发展. 随着自由基反应的迅猛发展, 研究者将其拓展到有机硅分子间环化反应, 硅的环化反应迎来了新的发展. 主要从过渡金属催化的硅环化反应、自由基引发的硅环化反应、C^＋离子引发的硅环化反应展开讨论, 最后对当前的研究进展进行了总结.

关键词: C—H官能团化, 有机硅烷, 不饱和键, 环化反应

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

引用此文

南宁, 吴双, 秦景灏, 李金恒. 基于硅烷化启动的环化反应研究进展[J]. 有机化学, 2023, 43(10): 3414-3453.

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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图/表 53

图1. 农用化学品、气味剂、药品、先进材料和工业化学品中的代表性硅环化合物

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

图式1. Pd和Cu协同催化的二羰基化苯环化反应

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

图式2. Pd和Cu协同催化的二羰基化苯环化反应机理

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

图式3. 钯/铜催化的3-乙酰氧基-1,4-烯的甲硅烷基化[5＋1]苯环化反应

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

图式4. 钯/铜催化的3-乙酰氧基-1,4-烯的甲硅烷基化[5＋1]苯环化反应机理

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

图式5. 钯催化的应变释放硅基交叉偶联环化反应

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

图式6. 钯催化的应变释放硅基交叉偶联环化反应机理

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

图式7. 钯催化环丙烯与苯甲硅烷环丁烷环化反应

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

图式8. 钯催化环丙烯与苯甲硅烷环丁烷环化反应机理

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

图式9. 钯催化(杂)芳烃与四硅烷的硅烷环化反应

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

图式10. 钯催化(杂)芳烃与四硅烷的硅烷环化反应机理

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

图式11. 钯催化2-碘芳烃(4＋4)环化为八元硅环

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

图式12. 钯催化2-碘芳烃[4＋4]环化为八元硅环机理

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

图式13. 钯催化的不对称二硅烷化反应

Scheme 13. Palladium catalyzed asymmetric silylation reaction

图式14. 钯催化的不对称二硅烷化反应

Scheme 14. Palladium catalyzed asymmetric silylation reaction

图式15. Me3SiSiMe2(On Bu)硅烷试剂用于重排反应合成不同的硅烷环

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

图式16. Me3SiSiMe2(On Bu)硅烷试剂用于重排反应合成不同的硅烷环

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

图式17. 钯催化的分子间硅基C(sp2)—C(sp3)交叉偶联硅烷环化反应

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

图式18. 钯催化不对称二氟环丙烯的甲硅烷基化

Scheme 18. Palladium catalyzed asymmetric methylsilylation of difluorocyclopropenes

图式19. 时间控制的钯催化级联C—H硅烷环化合成硅烷环反应

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

图式20. 钯催化级联C—H硅烷环化合成硅烷环反应机理

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

图式21. 铑催化的2 -芳基苯酚衍生的六元硅环化

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

图式22. 铑催化硅环丁烷(SCB)与未活化炔烃的环化反应

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

图式23. 铑催化硅环丁烷(SCB)与未活化炔烃的环化反应机理

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

图式24. 铑催化硅系双炔烃的选择性氢化硅烷化反应

Scheme 24. Selective hydrosilylation of silicone alkynes catalyzed by rhodium

图式25. 铑催化琥珀酰亚胺和吡唑酮基官能团1,6-二烯的螺环异构化反应

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

图式26. Rh/Cu催化不对称炔基酯与硅环丁烷的[4＋2]环化反应

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

图式27. Rh/Cu催化不对称炔基酯与硅环丁烷的[4＋2]环化反应机理

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

图式28. 铑催化的不对称硅氢化反应

Scheme 28. Asymmetric hydrosilylation catalyzed by rhodium

图式29. 铑催化4/5-螺硅芴与末端炔烃的不对称扩环反应

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

图式30. 铂催化2-(苯乙炔基)苯基甲醇的硅基环化反应

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

图式31. 铂催化2-(苯乙炔基)苯基甲醇的硅基环化反应机理

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

图式32. 钴不对称催化1,6-烯炔的氢化硅烷化/环化反应

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

图式33. 钴不对称催化1,6-炔烃的氢化硅烷化/环化反应机理

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

图式34. 铜催化2,2'-二苯乙烯基二芳基衍生物的硅烷化环化反应

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

图式35. 铜催化2,2′-二苯乙烯基二芳基衍生物的硅烷化环化反应机理

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

图式36. 可见光催化硅烷基碘和苯基炔烃的自由基环化反应

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

图式37. 可见光催化硅烷基碘和苯基炔烃的自由基环化反应机理

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

图式38. 铁催化N-芳基丙酰胺与硅烷的螺环化反应

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

图式39. 铁催化N-芳基丙酰胺与硅烷的螺环化反应机理

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

图式40. Mn催化N-(2-氰基)丙烯酰胺和叔硅烷的分子间氧化自由基杂环化反应

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

图式41. Mn催化N-(2-氰基)-丙烯酰胺和叔硅烷的分子间氧化自由基杂环化反应机理

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

图式42. Cu催化的Si—H和甲硅烷基C(sp3)—H键的氧化自由基官能团化的分子间环化级联反应

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

图式43. Cu催化的Si—H和甲硅烷基C(sp3)—H键的氧化自由基官能团化的分子间环化级联反应机理

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

图式44. 曙红Y光催化1,6-烯炔和氢化硅烷的环化反应

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

图式45. 曙红Y光催化1,6-烯炔和氢化硅烷的环化反应机理

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

图式46. 甲硅烷基自由基引发的自由基加成-易位-环化反应

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

图式47. 三苯甲基阳离子引发苄基取代的乙烯基环丙烷与氢化硅烷的环化反应

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

图式48. 三苯甲基阳离子引发苄基取代的乙烯基环丙烷与氢化硅烷的环化反应机理

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

图式49. 三苯甲基阳离子引发、甲硅烷基离子促进的芳基取代等位烯的氢化硅烷化反应

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

图式50. 三苯甲基阳离子引发、甲硅烷基离子促进的芳基取代等位烯的氢化硅烷化反应机理

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

图式51. 交叉共轭多烯与甲硅烷基离子的Nazarov环化反应

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

图式52. 交叉共轭多烯与甲硅烷基离子的Nazarov环化反应机理

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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