过渡金属催化不饱和烃与有机金属试剂及CO 2的串联羧化反应研究进展

doi:10.6023/cjoc202007013

摘要/Abstract

二氧化碳(CO ₂)作为一碳合成子具有储量丰富、无毒无污染、绿色清洁等优点, 因此在有机化学领域使用CO ₂作为一碳合成子反应一直以来受到广泛的关注. 过渡金属催化不饱和烃与CO ₂反应合成羧酸是CO ₂作为一碳合成子的重要应用之一, 这类反应可以通过串联羧化的策略实现, 过渡金属催化不饱和烃先与有机金属试剂反应在原位生成新的有机金属试剂, 之后再与CO ₂完成羧化. 常用的有机金属试剂如格氏试剂、有机锌试剂和有机铝试剂均能够完成这类反应. 根据不饱和烃的类别, 并根据羧化反应的类型介绍过渡金属催化不饱和烃与有机金属试剂及CO ₂的串联羧化反应.

关键词: 二氧化碳, 不饱和烃, 羧化反应, 过渡金属催化, 有机金属试剂

Carbon dioxide (CO ₂), as a one-carbon synthon, has many advantages such as abundant, non-toxic, clean and so on. So the reactions using CO ₂ as a one-carbon synthon have been widely concerned in organic chemistry. Transition-metal- catalyzed reaction of unsaturated hydrocarbons with CO ₂ to produce carboxylic acid is one of the most commonly-used method to convert CO ₂, and organometallic reagents can be added to the reaction as reducing agent. This kind of reaction can be realized by the strategy of tandem reaction. In the reaction, the unsaturated hydrocarbons react with transition-metal catalysts and organometallic reagents to generate new organometallic reagents in situ first, and then complete carboxylation with CO ₂. Common organometallic reagents such as organozinc reagents, Grignard reagents, and organoaluminum reagents can all achieve this kind of carboxylation reaction. In this review, reactions are divided according to the type of unsaturated hydrocarbons, and each type can also be divided into hydrocarboxylation and carbocarboxylation. This review would introduce reaction according to this classification.

Key words: carbon dioxide, unsaturated hydrocarbons, carboxylation reaction, transition-metal catalysts, organometallic reagent

引用此文

易雅平, 杭炜, 席婵娟. 过渡金属催化不饱和烃与有机金属试剂及CO ₂的串联羧化反应研究进展[J]. 有机化学, 2021, 41(1): 80-93.

Yaping Yi, Wei Hang, Chanjuan Xi. Recent Advance of Transition-Metal-Catalyzed Tandem Carboxylation Reaction of Unsaturated Hydrocarbons with Organometallic Reagents and CO₂[J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 80-93.

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图/表 18

图式1. 过渡金属与烯烃和CO2的反应过程

Scheme 1. Reaction process of transition-metal with alkene and CO2

图式2. 串联羧化反应过程

Scheme 2. Reaction process of transition-metal-catalyzed tandem carboxylation reaction

图式3. 铁-铜协同催化的烯烃与CO2氢羧化反应

Scheme 3. Iron-copper cooperative catalyzed hydrocarboxylation of alkene with CO2

图式4. 铁催化苯乙烯与CO2高区域选择性氢羧化反应

Scheme 4. Iron-catalyzed high-regioselective hydrocarboxylation of styrene with CO2

图式5. Cp2TiCl2催化烯烃与CO2高区域选择性氢羧化反应

Scheme 5. Cp2TiCl2-catalyzed high-regioselective hydrocarboxylation of alkene with CO2

图式6. Cp2ZrCl2催化烯烃与乙基格氏试剂及CO2的乙基羧化反应

Scheme 6. Cp2ZrCl2-catalyzed ethylcarboxylation of alkene with ethyl-Grignard-reagent and CO2

Scheme 7. 铜催化2,3-累积双烯丙醇与CO2合成2,5-呋喃酮 Copper-catalyzed synthesis of 2,5-furanone from 2,3-allenols with CO2

图式8. 钛催化烯烃与卤化物和CO2的碳羧化反应

Scheme 8. Cp2TiCl2-catalyzed carbocarboxylation of alkene with halides and CO2

图式9. 镍催化炔烃与CO2的氢羧化反应

Scheme 9. Nickel-catalyzed hydrocarboxylation of alkynes with CO2

Scheme 10. 镍催化高炔丙醇与CO2立体选择性地合成α-亚烷基-γ-丁内酯

. Nickel-catalyzed stereoselective synthesis ofα-alkylidene-γ-butyrolactone from homopropargylic alcohols and CO2

Scheme 11. 镍催化2-炔基苯胺与CO2立体选择性地合成(E)-3-亚烷基-2-吲哚酮

. Nickel-catalyzed stereoselective synthesis of (E)-3-alkylidene-2-indolinones from 2-alkynylaniline and CO2

图式12. 镍催化二炔与CO2的立体区域选择性氢羧化反应

Scheme 12. Nickel-catalyzed stereo- and regio-selective hydrocarboxylation with alkynes and CO2

Scheme 13. 铁催化炔烃与CO2的氢羧化反应

. Iron-catalyzed hydrocarboxylation of alkynes with CO2

Scheme 14. 钛催化炔烃与CO2的氢羧化反应

. Titanium-catalyzed hydrocarboxylation of alkynes with CO2

Scheme 15. 镍催化高炔丙醇与CO2及二甲基锌的碳羧化反应

. Nickel-catalyzed carbocarboxylation of homopropargylic alcohols with CO2 and dimethylzinc

Scheme 16. 金属催化CO2与炔烃的甲羧化和氢羧化反应

. Metal-catalyzed methylcarboxylation and hydrocarboxylation of alkynes with CO2

Scheme 17. 镍催化炔烃与芳基镁试剂及CO2的碳羧化反应

. Nickel-catalyzed carbocarboxylation of alkynes with arylmagnesium reagents and CO2

图式18. 镍催化烯炔与CO2的高度选择性氢羧化反应

Scheme 18. Nickel-catalyzed high-selective hydrocarboxylation of enynes with CO2

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过渡金属催化不饱和烃与有机金属试剂及CO ₂的串联羧化反应研究进展

Recent Advance of Transition-Metal-Catalyzed Tandem Carboxylation Reaction of Unsaturated Hydrocarbons with Organometallic Reagents and CO₂

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