烯醇类化合物氧化偶联反应研究进展

doi:10.6023/cjoc202104058

摘要/Abstract

烯醇类化合物氧化偶联反应作为直接构建C—C键的高效合成方法之一, 是有机化学领域研究关注的重点. 尽管首例烯醇类化合物氧化偶联反应早在1935年就已被报道, 但直到20世纪70年代才得到化学家们的广泛重视, 不过当时反应的有效性和实用性仍有待进一步提高. 近年来, 该反应在有机合成方法学和天然产物全合成方面都取得了快速的发展. 因此, 重点概述了近十年来该类型反应合成方法学的发展及其在天然产物全合成的应用研究进展.

关键词: 氧化偶联反应, 烯醇类化合物, 碳碳键, 方法学, 天然产物

Oxidative coupling reaction of enol derivatives (enolates, enol silanes, enamines, etc.) provides an efficient method for the direct construction of carbon-carbon bond, which plays a prominent role in the field of synthetic chemistry. Although the first case of this reaction had been reported in 1935, it was not until the 1970s that chemists began to pay more attention to this reaction. However, the effectiveness and practicability of this reaction were still somewhat limited at that time. In recent years, this reaction has been developed rapidly in the field of synthetic methodology and the total synthesis of natural products. Therefore, these advances in methodologies and its applications in the total synthesis of natural products in the last decades are mainly summarized.

Key words: oxidative coupling reaction, enol derivatives, carbon-carbon bond, methodology, natural product

引用此文

陈伟, 刘强. 烯醇类化合物氧化偶联反应研究进展[J]. 有机化学, 2021, 41(9): 3414-3430.

Wei Chen, Qiang Liu. Recent Advances in the Oxidative Coupling Reaction of Enol Derivatives[J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3414-3430.

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图/表 41

图式1. 偶联反应的三种形式

Scheme 1. Three types of the coupling reaction

图式2. 烯醇类化合物氧化偶联反应的类型

Scheme 2. Oxidative coupling reaction of enol derivatives

图式3. 早期报道的烯醇形式底物交叉氧化偶联反应

Scheme 3. Oxidative cross-coupling reaction of enolates

Ketone A	Ketone B	Product C	A₂B₂/A₄+B₄	Product ratio	Yield/%

表1. Flower研究小组报道的烯醇锂盐聚集效应对交叉氧化偶联反应的影响a

Table 1. Flowers' studies on Li-enolate aggregation effects of oxidative cross-coupling reaction

图式4. 早期报道的立体选择性自身氧化偶联反应

Scheme 4. Enantioselective oxidative homo-coupling reaction of titanium enolates

图式5. 利用自身氧化偶联反应合成轴手性联苯酚

Scheme 5. Enantioselective synthesis of biphenol via oxidative homo-coupling reaction reported by Thomson's group

图式6. 首例对映选择性的交叉氧化偶联反应

Scheme 6. First enantioselective oxidative cross-coupling reaction of enolates reported by Alezra's group

图式7. 铜(II)催化下烯醇类化合物自身化偶联反应

Scheme 7. Copper-catalyzed oxidative homo-coupling reaction of enolates reported by Daugulis's group

图式8. 铜(II)或银(I)催化下多取代五元杂环的合成

Scheme 8. Copper or silver-catalyzed syntheses of tetrasubstituted furans, thiophenes and pyrroles reported by Wang's group Reaction conditions: AgF (10 mol%), air, xylene, 140 ℃, 4~10 h; SET (single electron transfer)

图式9. 铈(III)催化下烯醇类化合物交叉氧化偶联反应

Scheme 9. Cerium catalyzed oxidative cross-coupling reaction of enolates reported by Christoffers's group

图式10. 铁(III)催化下烯醇类化合物交叉氧化偶联反应

Scheme 10. Iron-catalyzed catalyzed oxidative cross-coupling reaction of enolates reported by Ohshima and Takashi's group

图式11. 催化形式下烯醇类化合物不对称电化学合成

Scheme 11. Catalytic asymmetric electrosynthesis of enantioenriched molecules from enolates reported by Meggers's group

图式12. 烯醇硅醚分子间交叉氧化偶联反应

Scheme 12. Intermolecular oxidative cross-coupling reaction of enol silanes reported by Ruzziconi's group

图式13. 首例双烯醇硅醚分子内氧化偶联反应

Scheme 13. First oxidative homo-coupling reaction of bis-enol silanes reported by Schmittel's group

图式14. Thomson对双烯醇硅醚分子内氧化偶联反应的研究

Scheme 14. Intramolecular oxidative coupling reaction of bis- enol silanes reported by Thomson's group

图式15. 立体选择性的双烯醇硅醚交叉氧化偶联反应

Scheme 15. Stereoselective oxidative cross-coupling reaction of bis-enol silanes reported by Yang and Gong's group

图式16. 锰(III)催化下烯醇硅醚的电化学合成反应

Scheme 16. Electrochemical, manganese-assisted C—C bond formation reported by Hilt's group

图式17. 电化学条件下烯醇硅醚分子间氧化偶联反应可能的机理

Scheme 17. Proposed reaction mechanism for the Mn(TPA) dichloride mediated reaction reported by Hilt's group

图式18. 烯胺和烯醇硅醚分子间交叉氧化偶联反应

Scheme 18. Intermolecular oxidative cross-coupling reaction of enamine and enol silane reported by Narasaka's group

图式19. 有机催化下对映选择性的交叉氧化偶联反应

Scheme 19. Enantioselective organocatalytic oxidative cross- coupling reaction reported by MacMillan's group

图式20. 可见光催化下烯胺的交叉氧化偶联反应

Scheme 20. Visible-light-promoted oxidative cross-coupling reaction of enamines reported by Akita and Koike's group

图式21. 利用烯胺自身氧化偶联反应一步合成吡咯

Scheme 21. Pyrroles synthesis via oxidative homo-coupling reaction of enamines reported by Jia's group

图式22. 不对称催化下α,β-不饱和醛γ位交叉氧化偶联反应

Scheme 22. Catalytic asymmetric oxidative γ-coupling of α,β- unsaturated aldehydes reported by Jørgensen's group

图式23. 硼烯醇化合物自身氧化偶联反应

Scheme 23. Oxidative homo-coupling of boron enolate reported by Hirao's group

图式24. 硼烯醇化合物交叉氧化偶联反应

Scheme 24. Oxidative cross-coupling of boron enolate reported by Hirao's group

图式25. 钒(V)催化下硼烯醇化合物交叉氧化偶联反应

Scheme 25. Oxovanadium(V)-catalyzed oxidative cross-cou- pling of boron enolates reported by Hirao's group

图式26. 天然产物(±)-wikstromol的全合成

Scheme 26. Total synthesis of (±)-wikstromol reported by Belletire's group

图式27. 天然产物(–)-bursehernin的全合成

Scheme 27. Total synthesis of (–)-bursehernin reported by Baran's group

图式28. hapalindoles、fischerindoles、welwitindoles家族天然产物的不对称全合成

Scheme 28. Enantiospecific total synthesis of hapalindoles, fischerindoles, welwitindoles reported by Baran's group

图式29. 天然产物maoecrytal V核心骨架的构建

Scheme 29. Synthesis of the core carbon skeleton of maoecrystal V reported by Baran's group

图式30. 天然产物bismurrayaquinone A的全合成

Scheme 30. Total synthesis of bismurrayaquinone A reported by Thomson's group

图式31. 天然产物lomaiviticin A、lomaiviticinB的结构

Scheme 31. Structures of lomaiviticin A and lomaiviticin B

图式32. lomaiviticins 家族天然产物核心骨架的合成

Scheme 32. Synthesis of the core ring system of lomaiviticins reported by Shair's group

图式33. lomaiviticins 家族天然产物糖苷配基的合成

Scheme 33. Enantioselective synthesis of lomaiviticins aglycon reported by Herzon's group

图式34. 天然产物(±)-folicanthine的全合成

Scheme 34. Total synthesis of (±)-folicanthine reported by Bisai's group

图式35. 天然产物propindilactone G的全合成

Scheme 35. Total synthesis of propindilactone G reported by Yang and Chen's group

图式36. 天然产物(±)-hirsutene的全合成

Scheme 36. Total synthesis of (±)-hirsutene reported by Cohen and Ramig's group

图式37. 天然产物stephacidin A、avrainvillamide和stephacidin B的全合成

Scheme 37. Total synthesis of stephacidin A, avrainvillamide and stephacidin B reported by Baran's group

图式38. 天然产物(±)-actinophyllic acid的全合成

Scheme 38. Total synthesis of (±)-actinophyllic acid reported by Overman's group

图式39. 两种不同类型的分子内氧化偶联反应在多个吲哚类生物碱全合成中的应用

Scheme 39. Oxidative coupling strategies for the synthesis of indole alkaloids reported by Ma's group

图式40. 天然产物(+)-7,20-diisocyanoadociane的全合成

Scheme 40. Total synthesis of (+)-7,20-diisocyanoadociane reported by Thomson's group

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