Recent advances in fixation of CO2 into organic carbamates through multicomponent reaction strategies

doi:10.1016/S1872-2067(21)64029-9

Abstract

Abstract:

Carbon dioxide (CO₂) is the main greenhouse gas and also an ideal C1 feedstock in organic synthesis because it is abundant, non-toxic, nonflammable, and renewable. The synthesis of organic carbamates using CO₂ as a phosgene alternative has attracted extensive attention because of the importance of carbamates in organic synthesis and in the pharmaceutical and agrochemical industries. In recent decades, many multicomponent reaction strategies have been designed for constructing different types of organic carbamate molecules. Most of these methods rely on the in situ generation of carbamate anions from CO₂ and amines, followed by reactions with other coupling partners. Synthetic strategies for acyclic carbamates include nucleophile-electrophile coupling, nucleophile-nucleophile oxidative coupling, difunctionalization of unsaturated hydrocarbons, and C-H bond functionalization. Strategies for the synthesizing cyclic carbamates include carboxylative cyclization of in situ-generated unsaturated amines and difunctionalization of unsaturated amines with CO₂ and other electrophilic reagents. This review summarizes the recent advances in the synthesis of organic carbamates from CO₂ using different multicomponent reaction strategies. Future perspectives and challenges in the incorporation of CO₂ into carbamates are also presented.

Key words: Carbon dioxide, Amines, Carbamate, Multicomponent reaction, Synthetic strategy

Lu Wang, Chaorong Qi, Wenfang Xiong, Huanfeng Jiang. Recent advances in fixation of CO₂into organic carbamates through multicomponent reaction strategies[J]. Chinese Journal of Catalysis, 2022, 43(7): 1598-1617.

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Figures/Tables 44

Scheme 1. Representative carbamate-bearing molecules and traditional methods for synthesizing organic carbamates.

Scheme 2. Reaction pathways for the synthesis of acyclic carbamates with CO2.

Scheme 3. Strategies for synthesizing acyclic carbamates from CO2 via carbamate anion intermediate.

Scheme 4. PEG-promoted synthesis of carbamates from alkyl halides, CO2, and amines.

Scheme 5. Cs2CO3-promoted coupling of alkyl halides, CO2, and amines.

Scheme 6. Cs2CO3-promoted coupling of phenacyl bromide with CO2 and amines.

Scheme 7. Cs2CO3-promoted synthesis of nitrile-containing carbamates.

Scheme 8. Ir-catalyzed enantioselective coupling of allyl chlorides, CO2, and amines.

Scheme 9. Pd-catalyzed coupling of allyl chlorides, CO2, and amines.

Scheme 10. CaC2-promoted coupling of alcohols, amines, and CO2.

Scheme 11. Au/Fe2O3-catalyzed coupling CO2, epoxides, and amines.

Scheme 12. K2CO3-promoted coupling of CO2, amines, and N-tosylhydrazones.

Scheme 13. Ag-catalyzed coupling of CO2, amines and α-diazoesters.

Scheme 14. Visible-light-driven coupling of CO2, amines, and α-diazoesters.

Scheme 15. Ir-catalyzed coupling between CO2, amines, and sulfoxonium ylides.

Scheme 16. DBU-promoted coupling of CO2, amines, and diaryliodonium salts.

Scheme 17. Cu-catalyzed oxidative coupling of CO2, amines, and arylboronic acids.

Scheme 18. Ru-catalyzed synthesis of vinyl carbamate from CO2 and alkynes.

Scheme 19. Ag-catalyzed coupling of CO2, amines, and aryloxyallenes.

Scheme 20. Pd-catalyzed coupling of allenyl ethers, aryl iodides, amines, and CO2.

Scheme 21. Pd-catalyzed regioselective coupling of CO2, amines, and allenes.

Scheme 22. Cu-catalyzed coupling of enynes, Togni’s reagent, CO2, and amines.

Scheme 23. Cu-catalyzed coupling of akenes, CO2, amines, and Togni’s reagent.

Scheme 24. TBAI-mediated coupling of 3-triflyloxybenzynes, cyclic ethers, amines, and CO2.

Scheme 25. Photocatalytic coupling of ethynylbenziodoxolones, CO2, and amines.

Scheme 26. TBAI-catalyzed oxidative coupling of aryl ketones, amines, and CO2.

Scheme 27. Cu-catalyzed coupling of amines, CO2, and pincer-like arenes.

Scheme 28. Cu-catalyzed coupling of aryl carboxamides, amines, and CO2.

Scheme 29. Strategies for the synthesis of cyclic carbamates from CO2 via multicomponent reaction.

Scheme 30. Cu-catalyzed coupling of aldehydes, terminal alkynes, amines, and CO2.

Scheme 31. CuI/SnCl2-cocatalyzed coupling of ketones, amines, alkynes, and CO2.

Scheme 32. Tandem reaction for the synthesis of chiral oxazolidinones.

Scheme 33. Ag-catalyzed coupling of N-iodosuccinimide, propargylic amines, and CO2.

Scheme 34. Pd-catalyzed coupling of propargylic amines, aryl halides, and CO2.

Scheme 35. Pd/Cu-catalyzed coupling of propargylic amides, aryl halides, and CO2.

Scheme 36. Metal-free coupling of unsaturated amines with t-BuOI and CO2.

Scheme 37. Cu-catalyzed oxy-trifluoromethylation of allylamines with CO2 and Togni’s reagent.

Scheme 38. Cu-catalyzed dearomatization of indoles and furans with Togni’s reagent and CO2.

Scheme 39. Cu-catalyzed oxy-cyanoalkylation of allylamines with cycloketone oxime esters and CO2.

Scheme 40. Visible-light-driven oxy-perfluoroalkylation of allylic amines with CO2 and perfluoroalkyl iodides.

Scheme 41. Visible-light-driven oxy-difluoroalkylation of allylic amines with CO2.

Scheme 42. Visible-light-driven Pd-catalyzed oxy-alkylation of allylic amines with alkyl bromides and CO2.

Scheme 43. Pd-catalyzed oxy-alkylation of 2,3-allenic amines, organic iodides, and CO2.

Scheme 44. Visible-light-driven Pd-catalyzed oxy-alkylation of 2-(1-arylvinyl)anilines with CO2 and alkyl bromides.

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Recent advances in fixation of CO₂into organic carbamates through multicomponent reaction strategies

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