过渡金属催化的硫酯的交叉偶联反应研究进展

doi:10.6023/A23010013

摘要/Abstract

硫酯在医药、农药、香精香料、材料等领域应用广泛, 可从羧酸衍生得到, 羧酸在自然界寻常可见、结构丰富. 硫酯C(O)—S键能轻易和低价过渡金属发生氧化加成生成C(O)—M—S, 该物种在不脱羰或脱羰情况下可以和亲核试剂反应构建碳碳键. 近二十年来, 人们广泛研究了过渡金属催化的硫酯的交叉偶联反应, 这为从羧酸出发构筑C—C键提供了可供选择的有效方案. 本综述按照过渡金属种类, 依次对钯、镍、铜、铑等过渡金属催化的硫酯的交叉偶联反应进行了总结和讨论, 综述了该类反应在天然产物、药物分子合成及其后期转化中的应用. 同时关注了近些年报道的硫酯的不对称交叉偶联反应, 以及硫酯的交叉偶联反应在串联反应和官能团转化方面的应用.

关键词: 硫酯, 羧酸衍生物, 过渡金属催化, 交叉偶联反应, 脱羰

Thioesters with intriguing chemistry and reactivity are widely used in pharmaceuticals, pesticides, perfume & flavors and materials. Thioesters are versatile building blocks in organic synthesis and are also often employed as electrophilic acylating reagents in substitution reactions, such as Corey-Nicolaou macrolactonizations and native chemical ligation for peptide connection. Thioesters can be easily obtained from direct thioesterification of carboxylic acids with various thiol sources. Whereas more efforts have been made to develop new reactions employing thioesters, their application in organic synthesis is rare compared with other carboxylic acid derivatives. Transition-metal-catalyzed C—S bond activation paves a new avenue to exploit thioester. Many new transformations have been developed, including reduction to aldehydes, decarbonylation to thioethers, addition to unsaturated bonds, and cross-coupling of thioesters with organometallic reagents. Compared with other carboxylic acid derivatives, thioesters are stable but reactive and could undergo the oxidative addition of C(O)—S to low-valent transition-metal species, generating the C(O)—M—S. Transition-metal-catalyzed cross-coupling reaction of thioesters have been extensively studied in the last two decades, and providing alternative and efficient ways to construct C—C bonds. Despite the reaction between thioester and selected organometallic reagents to furnish ketones, thioesters could also be employed as decarbonylative coupling electrophiles. The advances in transition-metal-catalyzed cross-coupling reaction of thioesters are summarized in this review, which is presented by the categories of transition metals including Pd, Ni, Cu and Rh. Simultaneously, synthetic applications of transition-metal-catalyzed cross-coupling reaction of thioesters in nature products and pharmaceuticals are discussed. Attention is also paid to the asymmetric cross-coupling reaction of thioesters reported in recent years, the application of cross-coupling reaction of thioesters in tandem reactions and functional group transformations.

Key words: thioester, carboxylic acid derivative, transition-metal-catalysis, cross-coupling reaction, decarbonylation

引用此文

韩明亮, 徐丽华. 过渡金属催化的硫酯的交叉偶联反应研究进展[J]. 化学学报, 2023, 81(4): 381-392.

Mingliang Han, Lihua Xu. Progress on the Transition Metal-catalyzed Cross-coupling Reaction of Thioesters[J]. Acta Chimica Sinica, 2023, 81(4): 381-392.

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图/表 35

图式1. 过渡金属催化的硫酯参与的反应

Scheme 1. Transition-metal-catalyzed reaction employing thioesters as substrates

图式2. 钯催化的硫酯的酰基交叉偶联反应机理

Scheme 2. Mechanism of Pd catalyzed acyl cross-coupling of thioesters

图式3. Fukuyama反应

Scheme 3. Fukuyama reaction

图式4. Fukuyama反应在phomoidride B和(＋)-Haplophytine全合成中的应用

Scheme 4. Fukuyama reaction and its application in the total synthesis of phomoidride B and (＋)-Haplophytine

图式5. Liebeskind-Srogl交叉偶联反应

Scheme 5. Liebeskind-Srogl cross-coupling reaction

图式6. Pd-NHC催化的Liebeskind-Srogl交叉偶联反应

Scheme 6. Pd-NHC catalyzed Liebeskind-Srogl cross-coupling reaction

图式7. 硫酯和烷基硼试剂的交叉偶联反应

Scheme 7. Cross-coupling of thioesters with aliphatic organoboron reagents

图式8. “一锅法”制备环酮

Scheme 8. One-pot synthesis of carbocyclic ketones

图式9. (－)-D-erythro-Sphingosine 19的全合成

Scheme 9. Total synthesis of (－)-D-erythro-Sphingosine 19

图式10. Verbenachalcone的全合成

Scheme 10. Total synthesis of verbenachalcone

图式11. 芳基硼酸的甲氧羰基化和氟代乙酰基化反应

Scheme 11. Methoxycarbonylation and fluoroacylation of arylboronic acid

图式12. 芳基硼酸酯的二羰基化反应

Scheme 12. Dicarbonylation of aryl borates

图式13. 硫酯和有机锡试剂的交叉偶联反应

Scheme 13. Cross-coupling of thioesters with organostannanes

图式14. 合成goniodomin A的C15－C36片段时中间体35的合成

Scheme 14. Synthesis of intermediate 35 in synthesis of the C15－C36 segment of goniodomin A

图式15. 合成amphidinolide C时重要中间体38的合成

Scheme 15. Synthesis of key intermediate 38 in synthesis of side chain of amphidinolide C

图式16. Litseaverticillol A 41的全合成

Scheme 16. Total synthesis of litseaverticillol A 41

图式17. Flueggeacosine B 44的全合成

Scheme 17. Total synthesis of flueggeacosine B 44

图式18. 硫酯和有机铟试剂的交叉偶联反应

Scheme 18. Cross-coupling of thioesters with organoindium reagents

图式19. 硫酯和有机硅试剂的交叉偶联反应

Scheme 19. Cross-coupling of thioesters with organosilanes

图式20. 硫鎓盐阳离子和有机硼试剂的交叉偶联反应

Scheme 20. Cross-coupling reaction of thioester sulfonium salts and organoboron

图式21. 硫酯和烯烃的分子内交叉偶联反应

Scheme 21. Intramolecular cross-coupling reaction between thioesters and olefins

图式22. 硫酯的分子内C—H/C—S交叉偶联反应

Scheme 22. Intramolecular C—H/C—S cross-coupling of thioesters

图式23. 苄基锌试剂和硫酯的立体汇聚式Fukuyama反应

Scheme 23. Stereoconvergent Fukuyama reaction of benzyl zinc reagents and thioesters

图式24. 硫脂的脱羰不对称去芳构化反应

Scheme 24. Decarbonylative asymmetric dearomatization reaction of thioesters

图式25. 硫酯的不对称酰化-氨甲酰化环化反应

Scheme 25. Asymmetric cyclizations of thioesters via acyl-carbamoylation

图式26. Pd/NBE/Cu催化的芳基卤代物邻位酰基化和原位硫醚化反应

Scheme 26. Pd/NBE/Cu-catalyzed ortho-acylation and ipso-thiolation reaction of aryl halides

图式27. 钯/NBE协同催化的硫酯的脱羰双官能团化反应

Scheme 27. Palladium/norbornene-catalyzed decarbonylative difunctionalization of thioesters

图式28. 用于合成酮的镍催化的交叉亲电偶联反应

Scheme 28. Ni-catalyzed cross-electrophile coupling for the synthesis of ketones

图式29. NHP酯和硫酯的脱羰交叉亲电偶联反应

Scheme 29. Decarboxylative cross-electrophile coupling of NHP esters with thioesters

图式30. 镍催化的Fukuyama反应及其在合成(＋)-biotin时的应用

Scheme 30. Ni-catalyzed Fukuyama reaction and its application in the synthesis of (＋)-biotin

图式31. 钯和镍催化的硫酯的脱羰自偶联反应

Scheme 31. Palladium- and nickel-catalyzed decarbonylative self- coupling of thioesters

图式32. 铜催化的空气氛围下硫酯和硼酸的交叉偶联反应

Scheme 32. Cu-catalyzed aerobic cross-coupling of thioesters with boronic acids

图式33. 铜催化的空气氛围下硫酯和硼酸的交叉偶联反应机理

Scheme 33. Mechanism of Cu-catalyzed aerobic cross-coupling of thioesters with boronic acids

图式34. 铜催化的空气氛围下硫酯和硼酸或锡试剂的交叉偶联反应

Scheme 34. Cu-catalyzed aerobic cross-coupling of thioesters with boronic acids or organostannanes

图式35. 铑催化的芳基硫酯的脱羰硼化

Scheme 35. Rhodium-catalyzed decarbonylative borylation of aromatic thioesters

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