Research Progress of O—H Insertion Reaction Based on Diazo Ester

doi:10.6023/cjoc202006014

Abstract

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

Cite this article

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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Fig. & Tab. 25

Figure 1. Representative drugs containing phenoxy esters

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

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

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

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

Scheme 5. General catalytic cycle reaction mechanism

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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基于重氮酯的O—H插入反应研究进展