Progress in Transition-Metal-Catalyzed Carbonylative Cycloadditions Using Carbon Monoxide

doi:10.6023/cjoc202310003

Abstract

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

Cite this article

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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Fig. & Tab. 45

Figure 1. Several selected carbon synthons

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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