Progress in the Synthesis of Pyrrole-2-carboxylate Catalyzed by Transition Metals

doi:10.6023/cjoc202006048

Abstract

Pyrrole-2-carboxylates exist widely in biologically active molecules and have many important applications in the field of medicine. Therefore, the synthesis of pyrrole-2-carboxylates has received extensive attention. The transition metal- catalyzed cycloaddition reactions are widely used in the synthesis of pyrrole skeletons and have the advantages of regio- selectivity. The formation methods of C—N bonds directed by transition metal ligand have some advantages, such as milder reaction conditions, higher atomic step economy, efficiency and selectivity. The reactions of [3+2], [4+1] and [2+2+1] cycloaddition are reviewed, and the reaction mechanism and application of pyrrole-2-carboxylate compounds are introduced under various transition-metal conditions. The prospects of the synthesis of pyrrole-2-carboxylates are also discussed.

Key words: pyrrole-2-carboxylate, transition metal catalysis, C—N bond formation

Cite this article

Ci Li, Mingrui Li, Yuxing Xie, Yang Yu, Fei Huang. Progress in the Synthesis of Pyrrole-2-carboxylate Catalyzed by Transition Metals[J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 594-610.

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Fig. & Tab. 35

Figure 1. Bioactive molecules containing pyrrole-2-carboxylate

Scheme 1. Modification with pyrrole-2-carboxylate as substrate

Scheme 2. Classical synthetic method of pyrrole

Scheme 3. Several types of ring-forming reactions for the synthesis of pyrrole-2-carboxylate

Scheme 4. Cu-catalyzed 1,3-dipolar cycloaddition reaction of bissulfonyl ethylene with α-imino acid ester

Scheme 5. Cu-catalyzed 1,3-dipolar cycloaddition reaction of sulfonyl ketene with α-imino acid ester

Scheme 6. Cu-Mn-catalyzed oxidative cyclization of amino acid esters

Scheme 7. Cu-catalyzed oxidative cyclization of amines, alkynyl esters and maleimides

Scheme 8. Possible mechanism for oxidative coupling of amines, alkyne esters and maleimides

Scheme 9. Cu-catalyzed 1,4-addition reaction of azide

Scheme 10. Possible mechanism for the formation of pyrrole tetracarboxylate

Scheme 11. Cu-catalyzed [3+2] cycloaddition of isocyanide with alkyne

Scheme 12. Possible mechanism for Cu-catalyzed cycloaddition reaction of isocyanides and alkynes

Scheme 13. Copper-catalyzed carbene insertion and ester migration for synthesis of polysubtituted pyrroles

Scheme 14. Mechanism experiment for the reaction of Cu-cata- lyzed carbene insertion into enaminone

Scheme 15. Ru-catalyzed construction of pyrrole-2-carboxylate using photooxidation

Scheme 16. Possible mechanism for Ru-catalyzed construction of pyrrole-2-carboxylate

Scheme 17. Au-catalyzed cyclization of propionate derivatives with isoxazole

Scheme 18. Possible mechanism for Au-catalyzed reaction of acetylenic acid ester and isoxazole

Scheme 19. Au-catalyzed cyclization of alkynylaziridines

Scheme 20. Au-catalyzed ring isomerization of oxime with acetylene dicarboxylate

Scheme 21. Ag-catalyzed aromatization tandem reaction

Scheme 22. Ag-catalyzed 1,3-dipolar cycloaddition of α-bromobenzenesulfonyl ethylene with α-imino acid ester

Scheme 23. Ag-catalyzed [2+2+1] cyclization of alkynyl esters with amines

Scheme 24. Ag-catalyzed mechanistic for the addition/oxidative cyclization reaction

Scheme 25. Cyclization reaction of activated isocyanate and acrylate

Scheme 26. AgOTf-catalyzed [4+1C] insertion reaction for selective synthesis of pyrrole

Scheme 27. Mechanism experiment for Ag-catalyzed reaction of enaminone with diazo ester

Scheme 28. Possible mechanism for Ag-catalyzed reaction of enaminone with diazo ester

Scheme 29. Rh-catalyzed cyclization of β-fluoro-pyrrole-2-carboxylate

Scheme 30. Metal-catalyzed intramolecular cyclization of azide acrylate

Scheme 31. Rh-catalyzed cyclization of isonitriles with carbonyl compounds

Scheme 32. Pd-catalyzed coupling cyclization of OBO-ketones and nitroaromatics

Scheme 33. Pd-catalyzed cyclization of internal alkynes and 2-amino-3-iodoacrylate derivatives

Scheme 34. Pd-catalyzed cyclic isomerization of methyl iodide dehydrogenated amino acid

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