利用硅氢加成反应催化转化二氧化碳研究进展

doi:10.6023/cjoc202210024

摘要/Abstract

减少CO₂的排放和转化利用空气中的CO₂一直以来都是科研工作者研究的一个热点. CO₂具有无毒、丰富及易得的特点, 是合成有机化合物的理想原料. 近年来, 硅氢化还原反应已经发展成为一种有效转化CO₂的方法, 可以在较温和的反应条件下将CO₂还原转化为甲酸盐、甲醛、甲醇和甲烷等具有利用价值的化学产品, 大大促进了CO₂的转化和利用. 总结了用于催化CO₂硅氢化还原反应催化体系的设计、合成与催化性能研究进展, 讨论了CO₂硅氢化还原的反应机理, 分析了各种催化剂体系的优势和缺点, 并对该领域未来的研究方向进行了展望.

关键词: 催化, 二氧化碳, 硅氢化还原

Reducing carbon dioxide emission and converting carbon dioxide from the air have always been a hot topic for researchers. Carbon dioxide is an ideal raw material for synthesizing organic compounds because of its good physical properties such as non-toxicity, abundance and easy availability. In recent years, hydrosilylation reaction has become an effective method to convert carbon dioxide into formate, formaldehyde, methanol, methane and other valuable chemical products under moderate conditions, which greatly promotes the conversion and utilization of carbon dioxide. The research progress on the design, synthesis and catalytic performance of catalytic systems used to catalyze the hydrosilylation for reduction of carbon dioxide is summarized and discussed. The reaction mechanism of hydrosilylation reduction of carbon dioxide is discussed, and the advantages and disadvantages of various catalyst systems are also analyzed. At last, the future research directions in this field are prospected.

Key words: catalysis, carbon dioxide, hydrosilylation

引用此文

宋姿洁, 刘俊, 白赢, 厉嘉云, 彭家建. 利用硅氢加成反应催化转化二氧化碳研究进展[J]. 有机化学, 2023, 43(6): 2068-2080.

Zijie Song, Jun Liu, Ying Bai, Jiayun Li, Jiajian Peng. Progress in Catalysis Transformation of Carbon Dioxide through Hydrosilylation[J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2068-2080.

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图/表 23

图式1. CO2硅氢化还原合成甲硅烷基甲酸酯、双(甲硅烷基)缩醛、甲氧基硅烷和甲烷途径[1]

Scheme 1. Hydrosilylation of carbon dioxide for methylsilyl formate, bis(methylsilyl)acetal, methoxysilane and methane[1]

图式2. Ir-NSN催化剂1催化CO2硅氢化还原反应[17]

Scheme 2. Hydrosilylation of CO2 catalyzed by Ir-NSiN 1[17]

图式3. Ir-NSiN催化剂2催化CO2硅氢化还原反应[20]

Scheme 3. Hydrosilylation of CO2 catalyzed by Ir-NSiN 2[20]

图式4. 铱配合物催化CO2硅氢化还原反应[22]

Scheme 4. Hydrosilylation of CO2 catalyze by iridium complex[22]

图式5. 铑配合物4催化CO2甲酰化反应机理[23]

Scheme 5. Mechanism of CO2 formylation catalyzed by rhodium complex 4[23]

图式6. 钯配合物6催化CO2硅氢化还原反应[25]

Scheme 6. Hydrosilylation of CO2 catalyzed by Pd complex 6[25]

图式7. Pd配合物7催化CO2硅氢化还原反应[26]

Scheme 7. Hydrosilylation of CO2 catalyzed by Pd complex 7[26]

图式8. CO2插入催化剂13的Co—H键示意图[33]

Scheme 8. Insertion of CO2 into the Co—H bond of complex 13[33]

图式9. 配合物14催化CO2硅氢化还原反应机理[37]

Scheme 9. Mechanism for hydrosilylation of CO2 catalyzedby complex 14[37]

图式10. 配合物15催化CO2硅氢化还原反应机理[38]

Scheme 10. Mechanism for hydrosilylation CO2 catalyzed by complex 15[38]

图式11. 铁配合物催化CO2硅氢化还原反应[43]

Scheme 11. Iron complex catalyzed hydrosilylation of CO2[43]

图式12. Fe催化的胺与CO2选择性N-甲基化和N-甲酰化反应[45]

Scheme 12. Fe catalyzed selective N-methylation and N-formyl- ation of amines with CO2[45]

图式13. 配合物16催化CO2硅氢化还原反应机理[47]

Scheme 13. Mechanism for hydrosilylation of CO2 catalyzed by complex 16[47]

图式14. 锰基配合物催化胺与PhSiH3还原CO2为甲酰胺[48]

Scheme 14. Mn-based complex catalytic reduction of CO2 to formamides using amines and PhSiH3[48]

图式15. 配合物19催化CO2硅氢化还原反应可能中间产物[52]

Scheme 15. Possible intermediates in hydrosilylation of CO2 catalyzed by complex 19[52]

图式16. 配合物20活化氢硅烷作用机理[53]

Scheme 16. Mechanism for complex 20 actived hydrosilane[53]

图式17. [B(C6F5)4]21, 22催化炔烃、苯甲醛和CO2的硅氢化还原反应[61]

Scheme 17. Hydrosilylation of alkyne, benzaldehyde and CO2 catalyzed by [B(C6F5)4] 21, 22 complexes[61]

图式18. 配体控制铜催化CO2还原形成甲胺和甲酰胺[66]

Scheme 18. Ligand-controlled reduction of CO2 to form methylamines and formamides catalyzed by Cu[66]

图式19. 铜络合物23催化CO2硅氢化还原反应[67]

Scheme 19. Cu hydrosilylation of CO2 catalyzed by complex 23[67]

图式20. 1,3,2-二氮膦催化胺、Ph2SiH2、CO2生成甲酰胺[73]

Scheme 20. 1,3,2-Diazaphospholene-catalyzed reduction of CO2 to formamides using amines and Ph2SiH2[73]

图式21. TBD催化N-芳基-2-烷基色胺与CO2一锅法合成螺吲哚/螺吲哚啉[80]

Scheme 21. TBD-catalyzed synthesis of spiroindoles/spiroindolines from N-aryl-2-alkyltryptamines and CO2 in a one-pot fashion[80]

图式22. p[VBTAm]Cl的合成[86]

Scheme 22. Synthesis of p[VBTAm]Cl[86]

图式23. 二氧化硅负载甲酸盐催化CO2硅氢化还原反应[87]

Scheme 23. Hydrosilylation of CO2 using silica-supported formate as catalyst [87]

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