Recent Advances of Minisci Reactions in Aqueous Solution

doi:10.6023/cjoc202401015

Abstract

Minisci reaction is a convenient method for the functionalization of C—H in electron-defficient N-heterocycles. Different substituents could be introduced onto heterocycles through Minisci reaction, such as alkyl, acyl, silyl and alkylthio, etc. Water is eco-friendly and an ideal medium in organic synthesis, which has been applied in Minisci reaction. Recent progress in Minisci reaction in aqueous solution is reviewed herein. Minisci reaction is a convenient method for the functionalization of electron-defficient N-heterocycles. Different substituents could be introduced onto heterocycles through Minisci reaction, such as alkyl, acyl, silyl and alkylthio, boryl, etc. Thus, Minisci reaction is a powerful toolbox for the synthesis of substituted N-heterocylces. Water is eco-friendly and an ideal medium in organic synthesis, which has been applied in Minisci reaction. Although water was used from the discovery of Minisci reaction, Minisci reaction in aqueous solution is still underdeveloped. The recent progress in Minisci reaction in aqueous solution, including alkylation, arylation and acylation, is reviewed according to different radical precursors.

Key words: Minisci reaction, radical, aqueous solution, heterocycle

Cite this article

Wengui Wang, Shoufeng Wang. Recent Advances of Minisci Reactions in Aqueous Solution[J]. Chinese Journal of Organic Chemistry, 2024, 44(7): 2136-2146.

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Fig. & Tab. 32

Scheme 1. Radical-tpye C—H functionalization

Scheme 2. Decarboxylative Minisci reaction promoted by AgNO3-(NH4)2S2O8 in aqueous solution

Scheme 3. Decarboxylative alkylation of pyrimidines with alkyl carboxylic acids in aqueous solution

Scheme 4. Silver-catalyzed difluoromethylation of heteroaromatic compounds in aqueous solution

Scheme 5. Silver-catalyzed difluoromethylarylation of heteroaromatic compounds in aqueous solution

Scheme 6. Minisci reactions using unprotected amino acids as radical precursors in aqueous solution

Scheme 7. Silver-catalyzed Minisci reactions using Selectfluor as oxidant in aqueous solution

Scheme 8. Minisci reactions without extrenal acid in aqueous solution

Scheme 9. Transition metal-free decarboxylative Minisci reaction of coumarins in aqueous solution

Scheme 10. Minisci reaction using oxalates as radical precursors in aqueous solution

Scheme 11. Visible light-catalyzed decarboxylative Minisci rea- ction in aqueous solution

Scheme 12. Visible light-catalyzed arylation of ethers in aqueous solution

Scheme 13. Visible light-catalyzed photocatalyst free arylation of ethers in aqueous solution

Scheme 14. Persulfate-enabled arylation of ethers in aqueous solution

Scheme 15. Visible light-catalyzed arylation of alcohols in aqueous solution

Scheme 16. Minisci reactions using tertiary cycloalkanols in aqueous solution

Scheme 17. Visible light-catalyzed heteroarylation of remote C—H in tertiary alcohols in aqueous solution

Scheme 18. Water-promoted visible light-catalyzed Minisci reactions using aldehydes as alkylating reagent

Scheme 19. Visible light-catalyzed arylation of amines in aqueous solution

Scheme 20. Visible light-catalyzed alkylation of N-heteroaro- matics in aqueous solution

Scheme 21. Mn(III)-promoted Minisci reaction of alkyl trifluoroborates and N-heteroaromatics in aqueous solution

Scheme 22. Visibile light-catalyzed Minisci reaction of alkyl trifluoroborates in aqueous solution

Scheme 23. Minisci reactions using 1,4-dihydropyridines as alkylating reagents in aqueous solution

Scheme 24. Trifluoromethylation of N-heteroaromatics in aqueous solution

Scheme 25. Fluoalkylation of N-heteroaromatics in aqueous solution

Scheme 26. Alkylation of N-heteroaromatics in aqueous solution

Scheme 27. Silver-catalyzed arylation of N-heteroaromatics in aqueous solution

Scheme 28. Visible light-catalyzed Minisci-tpye arylation in aqueous solution

Scheme 29. Minisci-tpye arylation using triazenes in aqueous solution

Scheme 30. Visible light-catalyzed decarboxylative Minisci-tpye acylation in aqueous solution

Scheme 31. Silver-catalyzed acylation of N-heteroaromatics using aldehydes in aqueous solution

Scheme 32. Visible light-catalyzed acylation of N-heteroaro- matics using alkynes in aqueous solution

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水溶液中的Minisci反应研究进展