Research Progress on Carbonylation Involving Name Reactions

doi:10.6023/cjoc202406043

Abstract

The carbonylation of carbon monoxide (CO) or carbon dioxide (CO₂) catalyzed by transition metals is one of the effective strategies to construct high-value added chemicals, such as aldehydes, esters, amides, carboxylic acids, alcohols, etc. This reaction combines C1 chemical and petrochemical industries closely with the advantages of “atomic economy” and environmental friendliness. The organic name reaction is an important tool for constructing complex organic molecules. Based on the importance of organic name reactions and the significant application of carbonylation in these reactions, the research progress in recent years through the development of new catalytic systems for carbonylation is reviewed, including Reppe reaction, carbonylation coupling reaction, Alper carbonylation reaction, Pauson-Khand reaction, Gattermann-Koch formylation reaction, Koch-Haaf carbonylation reaction, Semmelhack reaction, and Wakamatsu reaction. Finally, the development and difficulties of carbonylation in organic synthesis are discussed in order to provide reference for promoting the generation of new carbonylation processes and achieving industrial transformation.

Key words: carbonylation, carbon monoxide, organic name reaction, Reppe reaction, carbonylation coupling reaction, Pauson-Khand reaction

Cite this article

Yaowei Wang, Peng Wang, Huibing Shi, Chengfu Zhang, Deming Zhao, Guiai Yang, Yaozong Yan, Baolin Feng. Research Progress on Carbonylation Involving Name Reactions[J]. Chinese Journal of Organic Chemistry, 2025, 45(1): 104-135.

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Fig. & Tab. 58

Scheme 1. Application of carbonylation in organic name reactions

Scheme 2. Reppe reaction

Figure 1. Phosphine ligands in hydroesterification reactions

Scheme 3. Synthesis of adipic acid esters via palladium-catalyzed bi-alkoxycarbonylation of 1,3-dienes

Scheme 4. Synthesis of α,β-unsaturated esters by alkoxycarbonylation

Scheme 5. Highly selective alkoxycarbonylation of alkenes

Scheme 6. High-performance carbonylation of alkenes catalyzed by palladium-aryldiphosphine catalytic system

Scheme 7. Asymmetric hydroesterification of diarylmethyl carbinols or cyclopropenes

Scheme 8. Synthesis of esters

Scheme 9. Low-cost metal catalyzed alkoxycarbonylation of alkyl halides

Scheme 10. Pd-catalyzed hydroaminocarbonylation of alkenes with amines

Scheme 11. Iron-catalyzed hydroaminocarbonylation of alkynes with NH4HCO3

Scheme 12. Copper-catalyzed hydroaminocarbonylation

Scheme 13. Palladium-catalyzed inward isomerization hydroaminocarbonylation of alkenes

Scheme 14. Double carbonylation catalyzed by Pd

Scheme 15. Synthesis of carboxylic acids via hydroxycarbonylation of olefins

Scheme 16. Asymmetric double hydroxycarbonylation of alkynes to chiral succinic acids enabled by palladium relay catalysis

Scheme 17. Room-temperature palladium-catalyzed hydrocarboxylation of alkynes with high branched selectivity

Scheme 18. Carbonylative Suzuki cross-coupling reaction

Scheme 19. Carbonylative Suzuki cross-coupling reaction regulated by CataCXium A

Scheme 20. Pd-Pincer complex catalyzed three-component carbonylative Suzuki-Miyaura cross-coupling reaction

Scheme 21. Pd/NHC complexes for carbonylative Suzuki coupling reaction

Scheme 22. Pd-Sn heterobimetallic catalyst for carbonylative Suzuki, Sonogashira and aminocarbonylation reactions

Scheme 23. Carbonylative Heck cross-coupling reaction

Scheme 24. Enantioselective carbonylative Heck reaction of o-iodoanilines with allenes

Scheme 25. Enantioselective palladium-catalyzed domino carbonylative Heck esterification of o-iodoalkenylbenzenes with arylboronic acids

Scheme 26. Carbonylative Stille cross-coupling reaction

Scheme 27. Carbonylative Stille cross-coupling reaction catalyzed by Nickel under phosphine-free condition

Scheme 28. Carbonylative Negishi cross-coupling reaction

Scheme 29. Nickel-catalyzed allylic carbonylative coupling of alkyl zinc reagents with tert-butyl isocyanide

Scheme 30. Nickel-catalyzed carbonylative Negishi cross-coupling of unactivated secondary alkyl electrophiles

Scheme 31. Carbonylative Sonogashira cross-coupling reaction

Scheme 32. Synthesis of α,β-unsaturated alkyne ketone by carbonylative Sonogashira cross-coupling reaction

Scheme 33. Carbonylative Sonogashira reaction catalyzed by ionic palladium complex

Scheme 34. Electrochemical palladium-catalyzed oxidative Sonogashira carbonylation of arylhydrazines and alkynes

Scheme 35. Triazine-wingtips accelerated NHC-Pd catalyzed carbonylative Sonogashira cross-coupling reaction

Scheme 36. Palladium-catalyzed carbonylative Sonogashira/annulation reaction for synthesis of indolo[1,2-b]isoquinolines

Scheme 37. Alper carbonylation reaction

Scheme 38. Palladium-catalyzed double carbonylation approach to isatins from 2-iodoanilines

Scheme 39. Carbonylation of aryl iodides with amides: facile synthesis of cyclic and acyclic amides

Scheme 40. Carbonylation applied to the synthesis of benzimidazo[2,1-b]quinazolin-12-ones

Scheme 41. Pauson-Khand reaction

Scheme 42. Ruthenium-catalyzed Pauson-Khand reaction

Scheme 43. Rhodium-catalyzed Pauson-Khand reaction of 1,6- and 1,7-enynes

Scheme 44. Intra- or intermolecular Pauson-Khand reaction

Figure 2. Synthesis of small molecules by Pauson-Khand reaction

Scheme 45. Reductive aza-Pauson-Khand reaction of nitriles

Scheme 46. Gattermann-Koch formylation reaction

Scheme 47. Application of Gattermann-Koch formylation

Scheme 48. Electrophilic formylation of arenes by silylium ion mediated activation of CO

Scheme 49. Koch-Haaf reaction

Scheme 50. Application of Koch-Haaf reaction

Scheme 51. Semmelhack reaction

Scheme 52. Synthesis of Leucascandrolide A by using Semmelhack reaction

Scheme 53. Synthesis of callipeltoside C and 4-dehydroxydiversonol by using Semmelhack reaction

Scheme 54. Synthesis of Neopeltolide and Kumausallene by using Semmelhack reaction

Scheme 55. Synthesis of Leucascandrolide A by using Semmel- hack reaction

Scheme 56. Synthesis of N-acyl amino-acids by Wakamatsu rea- ction

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涉及人名反应的羰基化反应研究进展