Recent Advances for Hydration Reaction of Nitriles in Different Catalytic Systems

doi:10.6023/cjoc202007020

Abstract

Nitriles can be used to construct new carbon-carbon and carbon-hetero bonds which result in diverse products. Among them, amide groups can be found in a large variety of drugs, pesticides, natural products and key intermediates in organic synthesis. Among all the methods reported for the synthesis of amides, hydration reaction of nitriles has become one of the most widely used methods to obtain primary amides in both academia and industry. Conventional nitrile hydration generally involves the use of strong acids and bases which would cause some problems such as low yields, poor reaction selectivity and over hydrolysis of products to carboxylic acids. To overcome these disadvantages, achieve the hydration of nitriles efficiently and meet the requirements of green chemistry, different catalytic systems have been successfully developed, including transition metal complex catalysts, metal cationic catalysts, metal nanoparticle catalysts, ionic liquid catalysts and other types of catalysts. The hydration reaction of nitriles in these catalytic systems is reviewed and summarized, and the development prospect of this field is prospected.

Key words: nitrile, catalytic system, hydration reaction, amide

Cite this article

Yujie Xia, Dandan He, Wanqing Wu. Recent Advances for Hydration Reaction of Nitriles in Different Catalytic Systems[J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 969-982.

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Fig. & Tab. 30

Figure 1. Three kinds of Co(III)-complex catalysts

Figure 2. Coordination mode of catalyst 2 with acetonitrile

Scheme 1. [RuH2(PPh3)4]-catalyzed reaction mechanism for hydration reactions of nitriles

Scheme 2. (η5-C9H7)-Ru(dppm)H-catalyzed reaction mechanism for hydration reactions of nitriles

Scheme 3. [Ru(η6-arene)Cl2(PR3)]-catalyzed reaction mechanisms for hydration reactions of nitriles

Figure 3. Hydrogen-bond between the catalyst and the water molecule

Figure 4. Structure of [RhCl(COD){P(NMe2)3}]

Figure 5. Hydrogen-bond between the catalyst 24a and the water molecule

Scheme 4. Synthesis of the catalyst 29 and 30

Scheme 5. Complex 29-catalyzed reaction mechanism for the hydration reactions of nitriles

Figure 6. Structure of intermediate 37

Figure 7. Three “donor-acceptor” catalysts

Scheme 6. Hydration reactions of nitriles and α-hydroxynitriles

Figure 8. P'-Pt-P(Me2OH) angles in 38a, 38b and 38c

Scheme 7. CoBr2/PP3-catalyzed reaction mechanisms for hydration reactions of nitriles and N-Methylation reactions of amides

Scheme 8. Pd(OAc)2-catalyzed reaction mechanism for hydration reactions of nitriles

Scheme 9. InCl3-catalyzed reaction mechanism for hydration reactions of nitriles

Scheme 10. CuO-catalyzed reaction mechanism for hydration reactions of nitriles

Scheme 11. NiCl2?H2O-catalyzed reaction mechanism for hydration reactions of nitriles

Scheme 12. Three possible reaction mechanisms

Scheme 13. Pd(NO3)2-catalyzed reaction mechanism for hydration reactions of α-hydroxynitriles

Scheme 14. Pd NPs-catalyzed reaction mechanism for hydration reactions of nitriles

Scheme 15. Reaction mechanisms for hydration reactions of nitriles in neutral and alkaline conditions

Scheme 16. NR-MnO2-catalyzed reaction mechanism for hydration reactions of nitriles

Scheme 17. TBAH-catalyzed reaction mechanism for hydration reactions of nitriles

Scheme 18. [Nbdm]OH-catalyzed reaction mechanism for hydration reactions of nitriles

Scheme 19. K2CO3-catalyzed reaction mechanism for hydration reactions of nitriles

Scheme 20. CsOH-DMSO-catalyzed reaction mechanism for hydration reactions of nitriles

Scheme 21. KOtBu-catalyzed reaction mechanism for hydration reactions of nitriles

Scheme 22. Solvent effect of different substrates

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