Recent Advances in the Synthesis of Arylstannanes

doi:10.6023/A22030118

Acta Chimica Sinica ›› 2022, Vol. 80 ›› Issue (7): 956-969.DOI: 10.6023/A22030118 Previous Articles Next Articles

Review

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)

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

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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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Fig. & Tab. 38

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

Scheme 2. Traditional synthetic routes towards arylstannanes

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

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

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

Scheme 6. Stannylation reaction of aryl zirconium reagent

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

Scheme 8. Stannylation reaction of aryl electrophiles

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Scheme 34. Electrophotocatalysis stannylation of chlorobenzene with hexamethyldistannane

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

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

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

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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