不同催化体系下腈的水合反应研究进展

doi:10.6023/cjoc202007020

摘要/Abstract

腈可用于构建新的碳-碳、碳-杂原子键, 所得产物丰富多样. 酰胺基团广泛存在于医药、农药和天然产物中, 此外, 酰胺还是有机合成反应中重要的中间体. 在目前报道的酰胺类化合物的合成方法中, 腈的水合反应已成为学术界和工业界最广泛使用的获得初级酰胺类化合物的方法之一. 早期腈的水合反应中通常涉及强酸、强碱的使用, 但在该类反应体系下, 往往存在产率低及反应选择性差等问题, 且所得酰胺容易过度水解成羧酸. 为了克服这一局限实现腈的高效水合, 且满足绿色化学的要求, 近年来, 不同的催化体系相继被开发, 如过渡金属配合物催化剂、金属阳离子催化剂、金属纳米粒子催化剂、离子液体催化剂及其它类型催化剂. 对这些催化体系下腈的水合反应研究进行阐述和总结, 并对该领域的发展前景进行了展望.

关键词: 腈, 催化体系, 水合反应, 酰胺

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

引用此文

夏玉杰, 何丹丹, 伍婉卿. 不同催化体系下腈的水合反应研究进展[J]. 有机化学, 2021, 41(3): 969-982.

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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图/表 30

图1. 三种Co(III)配合物催化剂

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

图2. 催化剂2与乙腈的配位方式

Figure 2. Coordination mode of catalyst 2 with acetonitrile

图式1. [RuH2(PPh3)4]催化腈的水合反应机理

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

图式2. (η5-C9H7)-Ru(dppm)H催化腈的水合反应机理

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

图式3. [Ru(η6-arene)Cl2(PR3)]催化下腈的水合反应机理

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

图3. 催化剂与水分子之间形成的氢键

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

图4. [RhCl(COD){P(NMe2)3}]的结构

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

图5. 催化剂24a与水分子之间形成的氢键

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

图式4. 催化剂29和30的合成

Scheme 4. Synthesis of the catalyst 29 and 30

图式5. 配合物29催化的腈的水合反应机理

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

图6. 中间体37的结构

Figure 6. Structure of intermediate 37

图7. 三种“donor-acceptor”型催化剂

Figure 7. Three “donor-acceptor” catalysts

图式6. 腈和α-羟基腈的水合反应

Scheme 6. Hydration reactions of nitriles and α-hydroxynitriles

图8. 38a, 38b和38c中的P'-Pt-P(Me2OH)角

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

图式7. CoBr2/PP3催化的腈的水合反应和酰胺的N-甲基化反应机理

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

图式8. Pd(OAc)2催化的腈的水合反应机理

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

图式9. InCl3催化的腈的水合反应机理

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

图式10. CuO催化的腈的水合反应机理

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

图式11. NiCl2?H2O催化的腈的水合反应机理

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

图式12. 三种可能的反应途径

Scheme 12. Three possible reaction mechanisms

图式13. Pd(NO3)2催化的α-羟基腈的水合反应机理

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

图式14. Pd NPs催化的腈的水合反应机理

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

图式15. 在中性和碱性条件下腈的水合反应机理

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

图式16. NR-MnO2催化的腈的水合反应机理

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

图式17. TBAH 催化的腈的水合反应机理

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

图式18. [Nbdm]OH催化的腈的水合反应机理

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

图式19. K2CO3催化的腈的水合反应机理

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

图式20. CsOH-DMSO催化的腈的水合反应机理

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

图式21. KOtBu催化的腈的水合反应机理

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

图式22. 不同底物的溶剂效应

Scheme 22. Solvent effect of different substrates

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