基于重氮酯的O—H插入反应研究进展

doi:10.6023/cjoc202006014

摘要/Abstract

对近10年来均相过渡金属、非金属及多相催化剂催化重氮酯O—H插入反应的研究进展进行综述. 重点阐述了各类催化剂的结构、催化体系及其在药物研发和有机合成方面的应用. 底物重氮酯易于制备, 催化剂廉价易得, 反应过程中形成的卡宾中间体反应活性高, 因此O—H插入反应可在温和条件下发生, 高效构筑C—O键, 并获得可观的收率和对映选择性, 有利于手性药物的开发和合成. 最后, 对O—H插入反应及产物的绿色合成进行展望.

关键词: 重氮酯, O—H插入反应, C—O键, 均相催化, 多相催化

The research progress of O—H insertion reaction of diazo esters catalyzed by homogeneous transition metal, nonmetal and heterogeneous catalysts in the past 10 years is reviewed. The structures and catalytic systems of various catalysts and their applications in drug development and organic synthesis are described. The substrate diazo ester is easy to prepare, the catalyst is cheap and easy to obtain, and the carbenoid intermediate formed in the reaction process has high reactivity. Therefore, the O—H insertion reaction can occur under mild conditions with efficient construction of C—O bond in considerable yield and enantioselectivity, which is conducive to the development and synthesis of chiral drugs. Finally, transition-metal- catalyzed O—H insertion and green synthesis are prospected.

Key words: diazo ester, O—H insertion reaction, C—O bond, homogeneous catalysis, heterogeneous catalysis

引用此文

王飞雨, 张志朋, 黄菲. 基于重氮酯的O—H插入反应研究进展[J]. 有机化学, 2021, 41(1): 144-157.

Feiyu Wang, Zhipeng Zhang, Fei Huang. Research Progress of O—H Insertion Reaction Based on Diazo Ester[J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 144-157.

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图/表 25

图1. 几种有代表性的含苯氧基酯的药物

Figure 1. Representative drugs containing phenoxy esters

图式1. 由铁/螺环双噁唑啉催化的不对称O—H插入

Scheme 1. Asymmetric O—H insertion catalyzed by Iron/spiro dioxazoline

图式2. 四苯基卟啉氯化铁(III) [Fe(TPP)Cl]催化的O—H插入反应

Scheme 2. O—H insertion reaction catalyzed by tetraphenyl porphyrin ferric(III) chloride [Fe(TPP)Cl]

图式3. 重氮磷酸酯的铜催化O—H插入反应

Scheme 3. Copper-catalyzed O—H insertion reaction of diazo phosphonates

图式4. [Tp MsCu(thf)]及[Tp X Cu(L)]配合物催化的重氮酯与水的O—H插入反应

Scheme 4. O—H insertion reaction of diazo ester and water catalyzed by [Tp MsCu(thf)] and [Tp X Cu(L)] complex

图式5. 一般催化循环反应机理

Scheme 5. General catalytic cycle reaction mechanism

图式6. [TpMsCu(thf)]催化反应机理

Scheme 6. [TpMsCu(thf)] catalytic reaction mechanism

图式7. 手性螺环双噁唑啉钯配合物催化剂催化α-芳基重氮酯不对称插入酚类化合物的O—H键

Scheme 7. Asymmetric insertion of O—H bond ofα-aryl-diazo esters into phenol compounds catalyzed by the chiral spiro dioxazoline palladium complex

图式8. 双吡啶配体催化酚的不对称O—H插入反应

Scheme 8. Asymmetric O—H insertion of phenols catalyzed by dipyridine ligands

图式9. 手性2,2'-二咪唑配体不对称催化酚类化合物和芳基重氮酯的对映选择性O—H插入反应

Scheme 9. Enantioselective O—H insertion reactions of phenolic compounds and aryl diazo esters catalyzed by the chiral 2,2'-diimidazole ligand

图式10. 金、铜催化O—H插入反应的显著化学选择性

Scheme 10. Obvious chemoselectivity observed in O—H insertion reaction catalyzed by gold and copper

图式1. 合成金络合物催化O—H插入反应

Scheme 11. O—H insertion reaction catalyzed by the synthetic gold complex

图式12. 具有手性磷配体的均相双核银络合物催化的O—H插入反应

Scheme 12. O—H insertion reaction catalyzed by a homogeneous binuclear silver complex with chiral phosphorus ligands

图式13. [CpRu(CH3CN)3][PF6] (Cp=C5H5)和吡啶-亚胺/吡啶-噁唑林配体作为催化剂催化的α-重氮羰基化合物的分解

Scheme 13. Decomposition ofα-diazo carbonyl compounds catalyzed by [CpRu(CH3CN)3][PF6] (Cp=C5H5) and pyridine- imine/pyridine-oxazolin ligands

图式14. B(C6F5)3•nH2O催化的均相O—H插入反应及其反应机制

Scheme 14. Homogeneous O—H insertion reaction catalyzed by B(C6F5)3•nH2O and its proposed mechanism

图式15. 二氟硼酸脲催化的均相O—H插入反应及其反应机制

Scheme 15. Homogeneous O—H insertion reaction catalyzed by difluoroboronate urea and its proposed reaction mechanism

图式16. 铱卟啉金属-有机骨架的合成及O—H插入反应

Scheme 16. Synthesis of iridium porphyrin metal organic frame- work and O—H insertion reaction

图式17. Ir-PMOF-41(Hf)催化的O—H插入反应及其反应机制

Scheme 17. O—H insertion reaction catalyzed by Ir-PMOF-41(Hf) and its reaction mechanism

图式18. 非手性双铑络合物与手性螺环磷酸催化的重氮酮与酚的O—H插入反应

Scheme 18. O—H insertion of diazoketones with alcohols co-catalyzed by achiral dirhodium complexes and chiral spiro phosphoric acid

图式19. 非手性双铑络合物与手性磷酸或手性磷酰胺催化的O—H插入反应

Scheme 19. O—H insertion catalyzed by achiral dirhodium complexes and chiral phosphoric acids or chiral phosphoramides

图式20. HClO4-SiO2催化的O—H插入反应底物拓展

Scheme 20. Scope of substrates of O—H insertion reaction catalyzed by HClO4-SiO2

图式21. HClO4-SiO2催化的O—H插入反应机制

Scheme 21. Mechanism of O—H insertion reaction catalyzed by HClO4-SiO2

图式22. 重氮酯与厚朴酚的O—H插入反应

Scheme 22. O—H insertion reaction between diazo ester and magnolol

图式23. 重氮酯与和厚朴酚的O—H插入反应

Scheme 23. O—H insertion reaction between diazo ester and honokiol

图式24. SW-I催化重氮酯与酚类化合物的O—H插入反应可能的机制

Scheme 24. Proposed mechanism of the O—H insertion reaction between diazo esters and phenols catalyzed by SW-I

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