Research Progress on CO Surrogates in Carbonylation Reactions

doi:10.6023/cjoc202412012

Abstract

The “carbonyl” functional group of the products in carbonylation reactions usually comes from gas carbon monoxide (CO) or its surrogates. Although gas CO as carbonyl source has wider substrate scope and can achieve industrial production, it is toxic and flammable. CO surrogates have stable chemical properties, which are easy to obtain. The reaction process is easy to operate and the separation/post-treatment is simple. Therefore, CO surrogates provide a variety of powerful and promising tools for the carbonylative conversion and construction of diverse chemicals. This review summarizes and discusses the latest progress in synthesizing high value-added chemicals using CO surrogates (carbon dioxide, chloroform, carboxylic acids and their derivatives, carbonyl metal reagents, acyl chlorides, etc.) as carbonyl sources. Finally, the development prospects and existing difficulties of different carbonyl sources in carbonylation reactions were discussed, in order to provide reference for promoting the development of more novel CO surrogates.

Key words: carbonylation, CO surrogates, carbon dioxide, chloroform, carboxylic acid derivatives, carbonyl metal reagent, acyl chloride

Cite this article

Baolin Feng, Peng Wang, Deming Zhao, Guiai Yang, Yaozong Yan, Huibing Shi, Yaowei Wang. Research Progress on CO Surrogates in Carbonylation Reactions[J]. Chinese Journal of Organic Chemistry, 2025, 45(8): 2773-2795.

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Fig. & Tab. 57

Scheme 1. CO surrogates used in carbonylation reactions

Scheme 2. Palladium-catalyzed direct carboxylation of aryl bromides with CO2

Scheme 3. Efficient fluoride-catalyzed conversion of CO2 to CO at room temperature

Scheme 4. Highly efficient Ru-catalyzed N-formylation of amines with H2 and CO2

Scheme 5. Visible-light-driven reductive carboarylation of styrenes with CO2 and aryl halides

Scheme 6. Pd-catalyzed thiocarbonylation of alkyl iodides or alkenes

Scheme 7. Carbo-carboxylation of alkenes via intramolecular Heck carbonylation utilizing CO2 and hydrosilane

Scheme 8. Efficient activation and selective conversion of CO2

Scheme 9. Electrocatalytic cascade reaction for the synthesis of ketones using CO2 as CO surrogate

Scheme 10. Electrochemical E-selective semireductive dicarboxylation of aryl alkynes with CO2

Scheme 11. Palladium-catalyzed carbonylation of organic halides by chloroform and alkali

Scheme 12. Palladium-catalyzed aminocarbonylation of halo- substituted 7-azaindoles and other heteroarenes

Scheme 13. Pd-catalyzed Heck cyclization and in situ hydrocarboxylation

Scheme 14. Palladium catalyzed aroylation of NH-sulfoximines with aryl halides

Scheme 15. Palladium catalyzed carbonylative coupling for synthesis of arylketones and arylesters

Scheme 16. Pd-catalyzed synthesis of 2-amidoimidazo[1,2- a]pyridines

Scheme 17. Pd/C-catalyzed domino synthesis of urea derivatives using chloroform as CO source

Scheme 18. Direct access to α,β-alkynylamides via Pd-catalyzed carbonylation of terminal alkynes with amines using chloroform as the CO surrogate

Scheme 19. Palladium-catalyzed ligand-controlled selective synthesis of aldehydes and acids from aryl halides and formic acid

Scheme 20. Silacarboxylic acids as efficient CO releasing molecules: synthesis and application in Pd-catalyzed carbonylation reactions

Scheme 21. Organo-photoredox catalyzed and transition-metal catalyzed hydroformylation

Scheme 22. Oxalic acid as the in situ CO generator in Pd-cata- lyzed hydroxycarbonylation of arylhalides

Scheme 23. Pd-catalyzed regiodivergent hydrocarboxylation of olefins with oxalic acid

Scheme 24. Organocatalyzed carbonylation of alkyl halides driven by visible light

Scheme 25. Base-promoted carbonylative cyclization of propargylic amines

Scheme 26. Pd-catalyzed carbonylation of propargyl diols with primary amines for the synthesis of acids

Scheme 27. Pd-catalyzed hydroxycarbonylation of aryl and vinyl halides or triflates by acetic anhydride and formate anions

Scheme 28. Pd-catalyzed carbonylation of aryl, alkenyl, and allyl halides with phenyl formate

Scheme 29. Preparation of α,β-unsaturated esters and amides via Pd-catalyzed carbonylation of alkenyl tosylates

Scheme 30. Trichlorophenyl formate as CO surrogate: Pd-catalyzed carbonylation of aryl/alkenyl halides and triflates

Scheme 31. Pd-catalyzed Heck cyclization/carbonylation with formates: synthesis of azaindoline-3-acetates and furoazaindolines

Scheme 32. Pd-catalyzed carbonylation of (hetero)aryl, alkenyl and allyl halides by means of N-hydroxysuccinimidyl formate as CO surrogate

Scheme 33. Diethyloxalate as CO source for Pd-catalyzed ethoxycarbonylation of bromo- and chloroarene derivatives

Scheme 34. Visible-light-driven alkene dicarboxylation with formate and CO2 under mild conditions

Scheme 35. Amines in microwave-heated aminocarbonylation reactions under air

Scheme 36. Co2(CO)8 as CO source for the amino carbonylation of (hetero)aryl halides with highly deactivated (hetero)arylamines

Scheme 37. Reductive carbonylation of (hetero) aryl halides and triflates using cobalt carbonyl as CO source

Scheme 38. Light-driven three-component carbonylation of aryl halides

Scheme 39. Dearomative carbonylations

Scheme 40. Ru-catalyzed carbonylation of aromatic C—H bonds using acid chloride

Scheme 41. Zn-mediated reduction of oxalyl chloride forming CO and its application in carbonylations

Scheme 42. Generation of CO and its efficient incorporation in Pd-catalyzed aminocarbonylations

Scheme 43. Ni-catalyzed reductive arylacylation of alkenes toward carbonyl-containing oxindoles

Scheme 44. Pd-catalyzed chlorocarbonylation of aryl (pseudo)halides through in-situ generation of CO

Scheme 45. Ni-catalyzed highly selective reductive carbonylation using oxalyl chloride as the carbonyl source

Scheme 46. Nickel-catalyzed carbonylative coupling of vinyl triflates with alkyl bromides toward enones with oxalyl chloride as the carbonyl source

Scheme 47. Alcohols as CO/H2 sources in Ru-catalyzed hydroesterification

Scheme 48. Utilizing glycerol as CO-source in Pd-catalyzed alkoxycarbonylation of styrenes

Scheme 49. Rh-catalyzed Pauson-Khand-type reaction with aldehydes

Scheme 50. Hydroformylation of olefins with paraformaldehyde catalyzed by Rh complexes

Scheme 51. CO-free aminocarbonylation of aryl and alkenyl iodides

Scheme 52. Pd-catalyzed carbonylation of aryl halides with N-formylsaccharin as a CO Source

Scheme 53. Pd-catalyzed fluorocarbonylation using N-formyl- saccharin as CO source

Scheme 54. Copper-catalyzed carbonylative transformations of indoles with hexaketocyclohexane

Scheme 55. Metal-free C—H [5＋1] carbonylation of 2-alkenyl/pyrrolylanilines using dioxazolones as carbonylating reagents

Scheme 56. Light-activated CO donor for Pd-catalyzed and light-mediated carbonylation

Scheme 57. Pd-catalyzed difluorocarbene transfer enabled divergent synthesis of γ-butenolides and ynones from iodobenzene and terminal alkynes

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