Application of Carbonylation in the Synthesis of Bulk and Fine Chemicals

doi:10.6023/cjoc202301025

Abstract

The reaction between unsaturated/halogenated hydrocarbons and carbon monoxide to construct chemicals containing carbonyl modules has attracted much attention due to its advantages, such as atomic economy, environmental friendliness and high chemical/regional selectivity. The research progress in the synthesis of bulk and fine chemicals with industrial application prospects through the construction of new catalytic systems for carbonylation in recent years is summarized, including the synthesis of aldehydes through hydroformylation, esters through hydroesterification, amides through aminocarbonylation, alcohols through “hydroformylation hydrogenation” tandem reaction, as well as the synthesis of high value-added products such as acid anhydrides, ketones, and acyl halides. Finally, the development prospects and existing difficulties of carbonylation are discussed, hoping to provide reference for promoting the industrial application of carbonylation reactions.

Key words: carbonylation, carbon monoxide, bulk chemical, fine organic chemical, olefin, hydroformylation

Cite this article

Huibing Shi, Yaowei Wang, Peng Wang, Deming Zhao, Baolin Feng, Yaozong Yan, Guiai Yang. Application of Carbonylation in the Synthesis of Bulk and Fine Chemicals[J]. Chinese Journal of Organic Chemistry, 2024, 44(6): 1811-1830.

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Fig. & Tab. 38

Scheme 1. Application of carbonylation in the synthesis of high value-added chemicals

Scheme 2. Rh single-atom as highly regioselective catalyst for hydroformylation of olefins

Scheme 3. Rhodium-catalyzed chemo-, regio- and enantioselective hydroformylation of cyclopropyl-functionalized trisubstituted alkenes

Scheme 4. Hydroformylation catalyzed by unmodified cobalt carbonyl under mild conditions

Scheme 5. Rhodium-catalyzed formylation of unactivated alkyl chlorides

Scheme 6. [Rh(cod)Cl]2/PPh3 catalyzed highly selective and recyclable homogeneous hydroformylation of olefins regulated by Et3N as additive

Scheme 7. Direct synthesis of adipic acid esters via palladium-catalyzed carbonylation of 1,3-dienes

Scheme 8. Palladium-catalyzed asymmetric Markovnikov hydroxycarbonylation and hydroalkoxycarbonylation of vinyl arenes to synthesize 2-arylpropanoic acids and esters

Scheme 9. Nickel-catalyzed asymmetric hydroaryloxy- and hydroalkoxy-carbonylation of cyclopropenes

Scheme 10. Bifunctional ligand regulated palladium-catalyzed selective hydroesterification of aliphatic alkenes

Scheme 11. Iron-catalyzed alkoxycarbonylation of alkyl bromides via a two-electron transfer process

Scheme 12. Manganese-catalyzed alkoxycarbonylation of alkyl chlorides

Scheme 13. Highly selective anti-Markovnikov hydroesterification of alkenes under mild conditions

Scheme 14. Pd catalyzed high regioselective carbonylation of alkenes to synthesize linear and branched selenoesters

Scheme 15. Palladium-catalyzed Markovnikov hydroaminocarbonylation of 1,1-disubstituted and 1,1,2-trisubstituted alkenes for formation of amides with quaternary carbon

Scheme 16. Highly efficient Markovnikov hydroaminocarbonylation of alkenes and alkynes catalyzed by a “soluble” heterogeneous Pd catalyst

Scheme 17. Anti-Markovnikov hydroaminocarbonylation of alkenes with aromatic amines

Scheme 18. Copper-catalyzed carbonylation of alkyl halides to synthesize α-keto amides and alkyl halide amides

Scheme 19. Photoinduced five-component radical relay CF3-aminocarbonylation of alkenes

Scheme 20. Palladium catalyzed carbonylation between alkyl aromatic hydrocarbons and aldehyde imines to synthesize β-lactams

Scheme 21. Synthesis of diamides and amido-esters via Pd- catalyzed carbonylation.

Scheme 22. Synthesis of alcohol by cobalt-catalyzed visible- light-driven reductive hydroformylation

Scheme 23. Acid-promoted hydroformylative synthesis of alcohol with CO2 by ruthenium-cobalt dual catalytic system

Scheme 24. Synthesis of cyclic anhydrides via carbonylation of C—H bond activation of aliphatic acids

Scheme 25. Nickel-catalyzed carbonylation of esters

Scheme 26. Light-mediated synthesis of aliphatic anhydrides by Cu-catalyzed carbonylation of alkyl halides

Scheme 27. Enantioselective carbonylative Heck coupling reaction of o-iodoanilines with allenes

Scheme 28. Carbonylative coupling reaction of allylic alcohols and organoalanes catalyzed by Ni catalysis

Scheme 29. Nickel-catalyzed acylzincation of unsaturated hydrocarbons with organozincs and CO

Scheme 30. Site-selective carbonylation of arenes via C(sp2)—H thianthrenation to access 1,2-diarylethanones

Scheme 31. Synthesis of acyl fluorides catalyzed by visible light/palladium synergy

Scheme 32. A dual light-driven palladium catalyst: breaking the barriers in carbonylation reactions

Scheme 33. A visible light driven Ni catalyzed carbonylation to synthesize acid chlorides from alkyl halides

Scheme 34. Palladium-catalyzed regiodivergent hydrochlorocarbonylation of alkenes for formation of acid chlorides

Scheme 35. Cu-catalyzed carbonylative silylation of alkyl halides to synthesize acylsilanes

Scheme 36. Asymmetric alkoxy- and hydroxy-carbonylations of alkenes assisted by β-carbonyl groups

Scheme 37. Data science-enabled Pd catalyzed enantioselective aryl-carbonylation of sulfonimidamides

Scheme 38. Cobalt-catalyzed multicomponent carbonylation of olefins for efficient synthesis of β-perfluoroalkyl imides, amides, and esters

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