一氧化碳参与的过渡金属催化的插羰环加成反应研究进展

doi:10.6023/cjoc202310003

摘要/Abstract

作为一种高效构建环状分子的方法, 环加成反应一直以来备受合成化学家的青睐. 一氧化碳(CO)气体是一种商业易得且廉价的原料, 常作为“一碳”组分参与各种过渡金属催化的环加成反应. 近几十年来, 得益于金属有机化学的深入研究, CO气体参与的过渡金属催化的环加成反应得到了迅速发展. 此类插羰环加成反应之所以成为有机化学的研究前沿, 是因为它们不仅可以用于构建复杂的环状骨架, 还可以引入具有广泛衍生化能力的羰基官能团. 这篇文章旨在详细介绍CO气体参与的过渡金属催化的插羰环加成反应, 并按照不同反应类型进行梳理和总结.

关键词: 环状分子, 一氧化碳(CO)气体, 过渡金属催化, 插羰反应, 环加成反应

Transition-metal-catalyzed cycloadditions have been evolved as important and efficient methods to construct cyclic molecules. Among them, transition-metal-catalyzed cycloadditions using carbon monoxide (CO) gas as the 1C synthon provide their unique and powerful approaches to build various cyclic molecules within a carbonyl group, which either acts as an important functional group within the cycloadducts, or can be further elaborated to other functional groups. The tremendous advances in this field are introduced.

Key words: cyclic molecule, carbon monoxide (CO) gas, transition metal catalysis, carbonylation, cycloaddition

引用此文

李晨龙, 余志祥. 一氧化碳参与的过渡金属催化的插羰环加成反应研究进展[J]. 有机化学, 2024, 44(4): 1045-1068.

Chen-Long Li, Zhi-Xiang Yu. Progress in Transition-Metal-Catalyzed Carbonylative Cycloadditions Using Carbon Monoxide[J]. Chinese Journal of Organic Chemistry, 2024, 44(4): 1045-1068.

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图/表 45

图1. 一些不同碳合成子列举

Figure 1. Several selected carbon synthons

图式1. Pauson-Khand反应和hetero Pauson-Khand反应

Scheme 1. Pauson-Khand reaction and hetero Pauson-Khand reaction

图式2. Wender课题组报道的铑催化的[2+2+1]反应

Scheme 2. Rhodium-catalyzed [2+2+1] reactions reported by Wender group

图式3. 李桂根课题组和施敏课题组发展的铑催化的Pauson-Khand型反应及相关反应

Scheme 3. Rhodium-catalyzed Pauson-Khand-type reactions and related ones developed by Li and Shi group

图式4. CO参与的镍催化的[2+2+1]反应

Scheme 4. Nickel-catalyzed [2+2+1] reactions involving CO

图式5. 钌催化的[2+2+1+1]反应

Scheme 5. Ruthenium-catalyzed [2+2+1+1] reactions

图式6. 铑催化的[2+2+1+1]反应

Scheme 6. Rhodium-catalyzed [2+2+1+1] reactions

图式7. 铑催化的[2+2+2+1]反应

Scheme 7. Rhodium-catalyzed [2+2+2+1] reactions

图式8. 三元或四元杂环与CO的[3+1]或[4+1]环加成反应

Scheme 8. [3+1] or [4+1] cycloadditions of 3- or 4-membered heterocycles and CO

图式9. de Meijere课题组报道的钴催化的[3+1]反应

Scheme 9. Cobalt-catalyzed [3+1] reactions reported by de Meijere group

图式10. 铑催化的[3+1]反应

Scheme 10. Rhodium-catalyzed [3+1] reactions

图式11. Fukuyama和Ryu等实现的钌催化的[3+2+1]反应

Scheme 11. Ruthenium-catalyzed [3+2+1] reactions realized by Fukuyama and Ryu group

图式12. 环丙烷或环丙烯作为“三碳”组分参与的铑催化的[3+2+1]反应

Scheme 12. Rhodium-catalyzed [3+2+1] reactions involving cyclopropanes or cyclopropenes as 3C synthons

图式13. Chung课题组发展的铑催化的[3+2+1]反应

Scheme 13. Rhodium-catalyzed [3+2+1] reactions developed by Chung group

图式14. 张俊良课题组实现的[3+2+1]反应

Scheme 14. [3+2+1] reactions realized by Zhang group

图式15. 亚甲基环丙烷参与的[3+2+1]反应

Scheme 15. [3+2+1] reactions involving methylenecyclopropanes

图式16. Bower课题组发展的[3+1+2]环加成反应

Scheme 16. [3+1+2] cycloadditions developed by Bower group

图式17. Eaton课题组实现的铁催化的[4+1]反应

Scheme 17. Iron-catalyzed [4+1] reactions realized by Eaton group

图式18. Murai课题组发展的[4+1]环加成反应

Scheme 18. [4+1] cycloadditions developed by Murai group

图式19. 铑催化的[4+1]反应

Scheme 19. Rhodium-catalyzed [4+1] reactions

图式20. 铑和铂催化的乙烯基联烯与CO的[4+1]反应

Scheme 20. Rhodium- and platinum-catalyzed [4+1] reactions of vinylallenes and CO

图式21. 环丙烷封端的共轭二烯和CO的[4+1]环加成

Scheme 21. [4+1] cycloadditions of cyclopropyl-capped dienes and CO

图式22. 张俊良课题组发展的[4+1]环加成反应

Scheme 22. [4+1] cycloadditions developed by Zhang group

图式23. 涉及1,3-酰氧基迁移的铑催化的[4+1]反应

Scheme 23. Rhodium-catalyzed [4+1] reactions involving 1,3-acyloxy migration

图式24. 铑催化的[4+3]/[4+1]环加成

Scheme 24. Rhodium-catalyzed [4+3]/[4+1] cycloadditions

图式25. 余志祥课题组发展的[4+2+1]反应

Scheme 25. [4+2+1] reactions developed by Yu group

图式26. 由张力释放控制的[4+2+1]环加成反应

Scheme 26. Strain-release-controlled [4+2+1] cycloadditions

图式27. 钯催化的[4+4+1]反应

Scheme 27. Palladium-catalyzed [4+4+1] reactions

图式28. 钴催化的[5+1]反应

Scheme 28. Cobalt-catalyzed [5+1] reactions

图式29. 钌催化的[5+1]反应

Scheme 29. Ruthenium-catalyzed [5+1] reactions

图式30. Liebeskind课题组发展的[5+1]反应

Scheme 30. [5+1] reactions developed by Liebeskind group

图式31. 余志祥课题组发展的铑催化的[5+1]和[5+1]/[2+2+1]反应

Scheme 31. Rhodium-catalyzed [5+1] and [5+1]/[2+2+1] reactions developed by Yu group

图式32. 唐维平课题组发展的[5+1]反应

Scheme 32. [5+1] reactions developed by Tang group

图式33. 钯催化的[5+1]反应

Scheme 33. Palladium-catalyzed [5+1] reactions

图式34. 铱催化的[5+1]反应

Scheme 34. Iridium-catalyzed [5+1] reactions

图式35. Wender课题组发展的[5+2+1]反应

Scheme 35. [5+2+1] reactions developed by Wender group

图式36. 余志祥课题组发展的[5+2+1]反应及其后续转化

Scheme 36. [5+2+1] reactions developed by Yu group and their further transformations

图式37. Wender课题组发展的[5+1+2+1]反应

Scheme 37. [5+1+2+1] reactions developed by Wender group

图式38. Wender课题组完成的[6+1]反应

Scheme 38. [6+1] reactions accomplished by Wender group

图式39. Chung课题组使用铑催化剂完成的[6+1]反应

Scheme 39. Rhodium-catalyzed [6+1] reactions achieved by Chung group

图式40. Bower课题组发展的[6+1]环加成反应

Scheme 40. [6+1] cycloadditions developed by Bower group

图式41. 铑催化的乙烯基螺戊烷与CO的[6+1]环加成

Scheme 41. Rhodium-catalyzed [6+1] cycloadditions of vinylspiropentanes and CO

图式42. 铑催化的[7+1]反应

Scheme 42. Rhodium-catalyzed [7+1] reactions

图式43. Bower课题组发展的铑催化的[7+1]反应

Scheme 43. Rhodium-catalyzed [7+1] reactions developed by Bower group

图式44. 镍催化的形式[5+1+1]反应

Scheme 44. Nickel-catalyzed formal [5+1+1] reactions

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