芳基锡烷的合成研究进展

doi:10.6023/A22030118

化学学报 ›› 2022, Vol. 80 ›› Issue (7): 956-969.DOI: 10.6023/A22030118 上一篇下一篇

综述

芳基锡烷的合成研究进展

岳广禄^a, 魏婧瑶^a, 邱頔^a^,^*(), 莫凡洋^b^,^*()

a 天津师范大学化学学院天津市功能分子结构与性能重点实验室天津 300387
b 北京大学材料科学与工程学院北京 100871

投稿日期:2022-03-17 发布日期:2022-04-30
通讯作者: 邱頔, 莫凡洋

作者简介:

岳广禄, 天津师范大学化学学院有机化学专业研究生. 2020年于天津师范大学化学学院获得学士学位. 2020年进入天津师范大学化学学院邱頔课题组进行研究生阶段学习. 目前主要从事芳香环碳锡键的构筑过程研究.

魏婧瑶, 天津师范大学化学学院有机化学专业研究生. 2021年于安阳师范学院获得学士学位. 2021年进入天津师范大学化学学院邱頔课题组进行研究生阶段学习. 目前主要从事芳香环基本官能团的转化过程研究.

邱頔, 天津师范大学化学学院副教授、硕士生导师. 2010年于北京大学化学与分子工程学院获得学士学位, 2015年于北京大学化学与分子工程学院获得理学博士学位, 有机化学专业, 师从王剑波教授和张艳教授. 2015年进入天津师范大学化学学院工作. 目前主要从事芳香环的碳磷键、碳锡键构筑过程研究和芳香环基本官能团的转化过程研究.

莫凡洋, 北京大学材料科学与工程学院特聘研究员、博士生导师. 分别于2004年与2006年在北京理工大学获得学士与硕士学位(导师: 周智明教授). 2006至2010年就读于北京大学化学与分子工程学院, 获得有机化学博士学位(导师: 王剑波教授). 2010至2011年在美国Scripps研究所从事博士后研究(导师: 张庆海教授); 2011至2015年在美国德克萨斯州大学奥斯汀分校从事博士后研究(导师: 董广彬教授), 2015年回到北京大学开展独立研究. 莫凡洋课题组致力于发展基于联硼化合物修饰的半导体氧化物材料在能源转换、光催化等方面的研究; 同时运用人工智能和机器人技术, 加速有机化学学科发展, 提高合成化学在材料制备和药物开发中的基础作用.

基金资助:
天津市教委高等学校科技发展基金计划项目(2020KJ007)

Recent Advances in the Synthesis of Arylstannanes

Guanglu Yue^a, Jingyao Wei^a, Di Qiu^a(), Fanyang Mo^b()

a Tianjin Key Laboratory of Structure and Performance for Functional Molecules, College of Chemistry, Tianjin Normal University, Tianjin 300387, China
b School of Materials Science and Engineering, Peking University, Beijing 100871, China

Received:2022-03-17 Published:2022-04-30
Contact: Di Qiu, Fanyang Mo
Supported by:
Science & Technology Development Fund of Tianjin Education Commission for Higher Education(2020KJ007)

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摘要/Abstract

芳基锡烷化合物是参与构筑功能分子中芳基碳碳键和碳杂原子键的一类重要合成中间体. 其在药物化学、材料科学以及有机合成中都具有重要应用, 因此发展其高效新颖的合成方法具有重要的意义. 根据反应机理的类型, 综述了近些年来合成芳基锡烷的方法, 包括(1)芳香亲核试剂的锡化反应; (2)芳香亲电试剂的锡化反应; (3)过渡金属催化的锡化偶联反应; (4)芳基自由基中间体介导的锡化反应; (5)炔烃的环化和串联的锡化反应. 最后, 进一步分析了未来合成芳基锡烷的研究趋势.

关键词: 芳基锡烷, Stille交叉偶联, 锡化反应, 芳基自由基

Arylstannanes are highly valuable synthetic intermediates in constructing aryl carbon-carbon bonds and carbon-heteroatom bonds in functional molecules. These compounds have demonstrated great applications in medicinal chemistry, materials science and organic synthesis. Due to the synthetic value, development of efficient and novel methods to synthesize arylstannanes is of significant importance. According to the type of reaction mechanism, this content will illustrate the methods for synthesizing arylstannanes in recent years including (1) stannylation of aromatic nucleophiles; (2) stannylation of aromatic electrophiles; (3) transition-metal-catalyzed stannylation coupling reactions; (4) stannylation reactions mediated by aryl radical intermediates; (5) cyclization of alkynes and tandem stannylation. Finally, we further provide a perspective on the development direction of the synthesis of arylstannanes.

Key words: arylstannanes, Stille cross-coupling reaction, stannylation, aryl radical

引用此文

岳广禄, 魏婧瑶, 邱頔, 莫凡洋. 芳基锡烷的合成研究进展[J]. 化学学报, 2022, 80(7): 956-969.

Guanglu Yue, Jingyao Wei, Di Qiu, Fanyang Mo. Recent Advances in the Synthesis of Arylstannanes[J]. Acta Chimica Sinica, 2022, 80(7): 956-969.

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图/表 38

图式1. 芳基锡烷在合成天然产物[2d]与功能材料[3b]中的应用

Scheme 1. Application of arylstannanes in the synthesis of natural products[2d] and functional materials[3b]

图式2. 传统的芳基锡烷合成方法

Scheme 2. Traditional synthetic routes towards arylstannanes

图式3. 芳基格氏试剂与三丁基氯化锡在超声波下合成芳基锡烷

Scheme 3. Synthesis of arylstannanes with aryl Grignard reagents and tributyltin chloride under ultrasonic condition

图式4. 芳基格氏试剂与双(三丁基锡)氧化物在超声波下合成芳基锡烷

Scheme 4. Synthesis of arylstannanes with aryl Grignard reagents and bis(tributyltin) oxide under ultrasonic condition

图式5. 钴催化的卤苯与三丁基氯化锡一锅法合成芳基锡烷

Scheme 5. Cobalt-catalyzed one-pot synthesis of arylstannanes from halobenzene and tributyltin chloride

图式6. 芳基锆试剂的锡化反应

Scheme 6. Stannylation reaction of aryl zirconium reagent

图式7. 双三甲基硅基噻吩氧化物与双(三丁基锡基)氧化物的锡化反应

Scheme 7. Stannylation reaction of 2,5-bis(trimethylsilyl)thiophene 1,1-dioxide with bis(tributyltin) oxide

图式8. 芳基亲电试剂的锡化反应

Scheme 8. Stannylation reaction of aryl electrophiles

图式9. 三氟化硼乙醚介导的芳基三氮烯的锡化反应

Scheme 9. Stannylation of aryltriazenes mediated by boron trifluoride diethyl etherate

图式10. 无过渡金属参与的芳香季铵盐锡化反应

Scheme 10. Transition-metal-free stannylation of aryl ammonium salts

图式11. 无过渡金属参与的芳香锍盐锡化反应

Scheme 11. Transition-metal-free stannylation of aryl sulfonium salts

图式12. 过渡金属催化的芳基卤代物和联锡的交叉偶联反应

Scheme 12. Transition-metal-catalyzed stannylation of aryl halides with ditin compounds

图式13. 钯催化的吲哚衍生物与六丁基二锡的锡化反应

Scheme 13. Palladium-catalyzed stannylation of indole derivatives with hexabutyldistannane

图式14. 微波照射下芳基卤化物经钯催化锡化反应一锅法交叉偶联及无溶剂下锡化反应

Scheme 14. Palladium-catalyzed stannylation of aryl halides under microwave irradiation by one-pot cross-coupling and solvent-free stannylation

图式15. 钯催化的芳香亚磺酸钠与联锡试剂的脱硫偶联反应

Scheme 15. Palladium-catalyzed desulfitative coupling reaction of sodium arylsulfinates with distannanes

图式16. 钯催化的2-(三甲基硅基)三氟甲磺酸苯酯的碳锡化反应

Scheme 16. Palladium-catalyzed carbostannylation of 2-(trimethylsilyl) phenyl trifluoromethanesulfonate

图式17. 铜催化的2-(三甲基硅基)三氟甲磺酸苯酯的碳锡化反应

Scheme 17. Copper-catalyzed carbostannylation of 2-(trimethylsilyl)- phenyltrifluoromethanesulfonates

图式18. 铜催化2-(三甲基硅基)三氟甲磺酸苯酯的芳基锡化反应

Scheme 18. Copper-catalyzed arylstannylation of 2-(trimethylsilyl)- phenyl trifluoromethanesulfonates

图式19. 镍催化多氟代芳烃C—H键直接锡化反应

Scheme 19. Nickel-catalyzed C—H bond direct stannylation of polyfluorinated arenes

图式20. 镍催化的芳基卤化物与三丁基甲氧基锡烷的锡化反应

Scheme 20. Nickel-catalyzed stannylation of aryl halides with tributylmethoxystannane

图式21. 镍催化的特戊酸芳香酯与三甲基(三丁基锡基)硅烷的锡化反应

Scheme 21. Nickel-catalyzed stannylation of aryl pivalate with trimethyl(tributyltinyl)silane

图式22. 镍催化芳香羧酸酯与三甲基(三丁基锡基)硅烷的锡化反应

Scheme 22. Nickel-catalyzed stannylation of aromatic carboxylates with trimethyl(tributyltinyl)silane

图式23. 镍催化的芳香酰氟与三甲基(三丁基锡基)硅烷的脱羰锡化反应

Scheme 23. Nickel-catalyzed decarbonylative stannylation of acyl fluorides with trimethyl(tributyltinyl)silane

图式24. 钯催化的芳香酰氟与六甲基二锡的脱羰锡化反应

Scheme 24. Palladium-catalyzed decarbonylative stannylation of acyl fluorides with hexamethyldistannane

图式25. 钯催化的芳香酰氟的脱羰锡化反应机理

Scheme 25. Mechanism of palladium-catalyzed decarbonylative stannylation of acyl fluorides

图式26. 涉及芳基自由基中间体的SRN1机理制备芳基锡烷

Scheme 26. SRN1 mechanism towards the synthesis of arylstannanes involving aryl radicals

图式27. 紫外光照射下芳基三甲基铵盐与三甲基锡钠的锡化反应

Scheme 27. Stannylation of aryl ammonium salts with trimethylstannyl sodium salt under UV light irradiation

图式28. 紫外光照射下芳基磷酸酯与三甲基锡钠的锡化反应

Scheme 28. Stannylation of aryl phosphate ester with trimethylstannyl sodium salt under UV light irradiation

图式29. 可见光激发卤代苯的脱卤素锡化反应

Scheme 29. Visible-light-excited dehalogenation stannylation of aryl halides

图式30. 芳香胺经由芳基自由基中间体进行的桑德迈尔锡化反应

Scheme 30. Sandmeyer-type stannylation of aromatic amines via aryl radical intermediates

图式31. 由硝基取代苯胺合成三甲基锡基取代的芳基硼酸酯

Scheme 31. Synthesis of trimethylstannyl arylboronates from nitro- substituted anilines

图式32. 紫外光照射下芳基卤代烷和六甲基二锡制备芳基锡烷

Scheme 32. Synthesis of arylstannanes from aryl halides and hexamethyldistannane under UV irradiation

图式33. 可见光驱动芳基偶氮砜的锡化反应

Scheme 33. Visible-light-driven stannylation of arylazo sulfones

图式34. 光电催化氯苯与六甲基二锡的自由基锡化反应

Scheme 34. Electrophotocatalysis stannylation of chlorobenzene with hexamethyldistannane

图式35. 钯催化炔烯串联环化锡化反应

Scheme 35. Palladium-catalyzed cascade cyclization-stannylation of enynes

图式36. 金催化二炔烃串联环化锡化反应

Scheme 36. Gold-catalyzed cascade cyclization-stannylation of diyne

图式37. 银催化邻炔基苯胺衍生物串联环化锡化反应

Scheme 37. Silver-catalyzed cascade cyclization-stannylation of o-alkynylaniline derivatives

图式38. 自由基介导的串联环化锡化反应

Scheme 38. Radical-mediated cascade cyclization-stannylation reaction

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芳基锡烷的合成研究进展

Recent Advances in the Synthesis of Arylstannanes

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