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

doi:10.6023/cjoc202007013

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (1): 80-93.DOI: 10.6023/cjoc202007013 Previous Articles Next Articles

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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

易雅平^a, 杭炜^a, 席婵娟^a^,^b^,^*()

a 清华大学化学系生命有机磷化学及化学生物学教育部重点实验室北京 100084
b 南开大学元素有机化学国家重点实验室天津 300071

收稿日期:2020-07-04 修回日期:2020-08-14 发布日期:2020-09-09
通讯作者: 席婵娟
作者简介:
* Corresponding author. E-mail: cjxi@tsinghua.edu.cn
基金资助:
国家自然科学基金(21871163); 国家自然科学基金(91645120); 国家自然科学基金(21472106)

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

Yaping Yi^a, Wei Hang^a, Chanjuan Xi^a^,^b^,^*()

a MOE Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology, Department of Chemistry,Tsinghua University, Beijing 100084
b State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071

Received:2020-07-04 Revised:2020-08-14 Published:2020-09-09
Contact: Chanjuan Xi
Supported by:
the National Natural Science Foundation of China(21871163); the National Natural Science Foundation of China(91645120); the National Natural Science Foundation of China(21472106)

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

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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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Fig. & Tab. 18

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

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

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

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

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

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

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

Scheme 9. Nickel-catalyzed hydrocarboxylation of alkynes with CO2

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

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

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

. Iron-catalyzed hydrocarboxylation of alkynes with CO2

. Titanium-catalyzed hydrocarboxylation of alkynes with CO2

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

. Metal-catalyzed methylcarboxylation and hydrocarboxylation of alkynes with CO2

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

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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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