Recent Advances on Carbonylation of 1,3-Dienes

doi:10.6023/cjoc202105036

Abstract

1,3-Butadiene is the main component of C₄ fraction in naphtha cracking process. The products of 1,3-butadiene carbonylation (hexanedial, adipic acid and dimethyl adipate) can be used in the production of nylon, plasticizer and pharmaceutical intermediates. How to efficiently and high chemo-/regio-selectivity synthesize these high value-added products has always been a difficult problem in organic chemistry research and industrial production. In this paper, the research progress of carbonylation (hydroformylation, hydroesterification, hydrocarboxylation) of 1,3-dienes (especially 1,3-butadiene) to construct high value-added chemicals in recent years is reviewed, then the difficulties and future development of this method are prospected.

Key words: 1,3-butadiene, hydroformylation, hydroesterification, syngas, homogeneous catalysis

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Peng Wang, Da Yang, Huan Liu. Recent Advances on Carbonylation of 1,3-Dienes[J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3379-3389.

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Fig. & Tab. 26

Figure 1. Homogeneously catalyzed 1,3-diene functionalization

Scheme 1. Hydroformylation of 1,3-butadiene and subsequent transformations

Scheme 2. Hydroformylation of 1,3-butadiene with transient protection of the first incorporated carbonyl group as acetal

Scheme 3. Selective hydroformylation of open-chain conjugated dienes promoted by mesitylene-solvated rhodium atoms to give β,γ-unsaturated monoaldehydes

Scheme 4. Formation of 1,6-hexanedial via hydroformylation of 1,3-butadiene by using different ligands

Scheme 5. Rh-catalyzed reductive hydroformylation of 1,3- butadiene

Scheme 6. Regioselective hydroformylation of butadiene: density functional studies

Scheme 7. Rhodium-catalyzed bis-hydroformylation of 1,3-butadiene to adipic aldehyde at low pressure

Scheme 8. Crotyl intermediates in Rh-catalyzed hydroformylation of 1,3-butadiene

Scheme 9. Density functional investigations of the Rh-catalyzed hydroformylation of 1,3-butadiene with bisphosphite ligands

Scheme 10. Rhodium-catalyzed hydroformylation of 1,3-buta- diene to adipic aldehyde

Scheme 11. Isomerizing hydroformylation of pent-3-enal

Scheme 12. Synthesis of adipic acid, 1,6-hexanediol and 1,6-hexanediamine via double?n?selective hydroformylation of 1,3-butadiene

Scheme 13. Hydroformylation of 1,3-diene

Scheme 14. Rh-catalyzed hydroformylation of 1,3-butadiene and pent-4-enal to adipaldehyde in CO2?expanded media

Scheme 15. Direct synthesis of adipic acid esters via palladium- catalyzed carbonylation of 1,3-dienes

Scheme 16. Efficient palladium-catalyzed carbonylation of 1,3- dienes

Scheme 17. Ni-catalyzed site-selective dicarboxylation of 1,3- dienes with CO2

Scheme 18. Hydroformylation of conjugated dienes catalyzed by cobalt

Scheme 19. Hydroformylation of isoprene

Scheme 20. Hydroformylation of 1,5-hexadiene to pimelaldehyde

Scheme 21. Regioselective rhodium-catalyzed hydroformylation of 1,3-dienes to highly enantioenriched β,γ-unsaturated aldehydes

Scheme 22. Influence of the reaction time on chemo- and enantioselectivity in the hydroformylation of 1-phenyl-1,3-butadiene

Scheme 23. Differences in the hydroformylation of 1,3-butadiene and 1,3-pentadiene

Scheme 24. Hydroformylation of cyclopentadiene

Scheme 25. Hydroformylation of piperylene

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1,3-二烯烃的羰基化反应研究进展