二氧化碳参与的三组分偶联反应进展

doi:10.6023/cjoc202309013

摘要/Abstract

二氧化碳(CO₂)是一种有吸引力的绿色可再生C1资源, 将其作为反应原料或者促进剂直接参与有机合成反应, 是绿色化学所倡导的研究方向. 另一方面, 三组分偶联反应被认为是合成化学中最具吸引力的策略之一, 它能够以简单易得的原料直接合成复杂分子. 基于此, 综述了将CO₂作为原料或促进剂, 参与的三组分偶联的反应体系, 以反应生成的产物类型进行分类: 羧基、酯基、羰基、烷基和氰基等一系列化合物以及CO₂作为促进剂的反应体系, 并对此类反应的发展做出展望.

关键词: 二氧化碳, 绿色化学, 三组分偶联, 促进剂

Carbon dioxide (CO₂) is the attractive green and renewable C1 resource, and its direct participation in organic synthesis reactions as a reaction feedstock or promoter, which is a research direction advocated by green chemistry. On the other hand, the three-component coupling reaction is considered to be one of the most attractive strategies in synthetic chemistry, which is capable of synthesizing complex molecules directly from simple and readily available raw materials. Based on this, this paper reviews the three-component coupling reaction systems involving CO₂ as a raw material or promoter, categorizes them according to the types of products generated: carboxyl, ester, carbonyl, haloalkyl, and cyano compounds as well as CO₂ as a promoter. An outlook on the development of such reactions is also given.

Key words: carbon dioxide, green chemistry, three-component coupling, promoter

引用此文

夏坤, 张开发, Sher Wali Khan, 阿布力米提•阿布都卡德尔. 二氧化碳参与的三组分偶联反应进展[J]. 有机化学, 2024, 44(5): 1506-1525.

Kun Xia, Kaifa Zhang, Sher Wali Khan, Abdukader Ablimit. Advances in Three-Component Coupling Reactions Involving CO₂[J]. Chinese Journal of Organic Chemistry, 2024, 44(5): 1506-1525.

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图/表 30

图1. CO2参与的三组分偶联反应

Figure 1. Heterocyclic compounds from new cyclization reactions using CO2

图式1. 醚与CO2和H2合成高级羧酸

Scheme 1. Synthesis of higher carboxylic acids from ethers with CO2 and H2

图式2. 酮或醛与CO2和H2合成高级羧酸

Scheme 2. Synthesis of higher carboxylic acids from ketone or aldehyde with CO2 and H2

图式3. 电催化下利用CO2和水进行苯乙烯的β-选择性羧化反应

Scheme 3. Electrochemical β-selective hydrocarboxylation of styrene using CO2 and water

图式4. 光催化下烯烃与CO2和甲酸盐的二羧化反应

Scheme 4. Photocatalytic dicarboxylation of olefins with CO2 and formates

图式5. 可见光驱动的铁促进烯烃和 CO2的硫代羧化反应

Scheme 5. Visible light-driven iron-promoted thiocarboxylation of olefins with CO2

图式6. 可见光驱动烯烃与CO2发生的氨基羧化

Scheme 6. Aminocarboxylation of visible light-driven olefins with CO2

图式7. 可见光氧化催化未活化烯烃与CO2的远程双官能化羧化反应

Scheme 7. Visible photooxidation-catalyzed remote difunctionalized carboxylation of unactivated olefins with CO2

图式8. 芳基镁试剂、CO2和炔烃反应生成三取代丙烯酸

Scheme 8. Arylmagnesium reagent, reaction of CO2 with alkynes to form trisubstituted acrylic acid

图式9. CO2在DES溶剂中合成氨基甲酸酯

Scheme 9. Synthesis of carbamate from CO2 in DES solvent

图式10. 亚胺和芳基酮对CO2的电催化固定

Scheme 10. Electrocatalytic immobilization of CO2 by imines and aryl ketones

图式11. 镍和光催化CO2合成芳基氨基甲酸酯

Scheme 11. Nickel and photocatalytic CO2 synthesis of aryl carbamates

图式12. 重氮化合物与CO2发生C(sp2)—H键直接酯基化反应

Scheme 12. Direct C(sp2)—H bond esterification of diazo couples with CO2

图式13. 光催化高价碘化合物、CO2和胺的偶联反应

Scheme 13. Photocatalytic coupling of ethynylbenziodoxolones, CO2 and amines

图式14. 可见光驱动未活化烷基溴和CO2催化苯胺的氧烷基化

Scheme 14. Visible light driven reactive alkyl bromine and CO2 catalyzed oxygen alkylation of aniline

图式15. 芳烃和CO2的[2＋2＋2]环化

Scheme 15. [2＋2＋2] cyclization of aromatic hydrocarbons and CO2

图式16. 协同氧化还原活化的CO2转化

Scheme 16. CO2 conversion through synergistic redox activation

图式17. CO2与吡啶衍生物的三组分反应

Scheme 17. Three component reaction between CO2 and pyridine derivatives

图式18. 钯催化CO2与异氰化物生成酮杂环

Scheme 18. Palladium catalyzed formation of ketone heterocycles from CO2 and isocyanides

图式19. CO2与芳胺、硫合成噻唑烷胺

Scheme 19. Synthesis of thiazolidine amine from CO2, aromatic amine, and sulfur

图式20. CO2在钒催化作用下合成不对称脲

Scheme 20. Synthesis of asymmetric urea with CO2 catalyzed by vanadium

图式21. 将CO2还原为亚甲基再生成二硫缩醛化合物

Scheme 21. Reducing CO2 to methylene and regenerating it into disulfide acetal compounds

图式22. 温和的条件下CO2与苯胺的N-甲基化反应

Scheme 22. N-Methylation reaction of CO2 with aniline under mild conditions

图式23. N-杂环亚胺作为亲核试剂催化胺与CO2的偶联反应

Scheme 23. N-heterocyclic imines as nucleophilic reagents catalyze the coupling reaction of amines with CO2

图式24. BICAAC催化CO2参与酰胺的N-甲基化反应

Scheme 24. BICAAC catalyzed CO2 participation in N-methylation of amides

图式25. CO2与芳胺和烯胺酮的一锅法N-甲基化?环化反应

Figure 25. One pot N-methylation cyclization reaction of CO2 with aromatic amines and ketene

图式26. CO2与NH3参与的芳基卤化物的选择性氰化

Scheme 26. Selective cyanidation of aryl halides involving CO2 and NH3

图式27. CO2与NH3参与的芳基卤化物的选择性氰化

Scheme 27. Selective cyanidation of aryl halides involving CO2 and NH3

图式28. CO2促进的三组分斯特里克反应

Scheme 28. Three component streak reaction promoted by CO2

图式29. 光和CO2催化非活性芳香胺的硼基化

Scheme 29. Boronization of non active aromatic amines catalyzed by light and CO2

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