铜催化不饱和化合物硅加成反应的研究进展

doi:10.6023/cjoc202207043

摘要/Abstract

有机硅化合物不仅是十分有用的功能分子, 而且是非常重要的有机合成中间体, 在一定条件下通过适当的化学方法, 可以转化为很多其它有用的功能性化合物. 到目前为止, 已经陆续发展了各种过渡金属参与的催化方法来制备有机硅化合物, 其中铜催化不饱和化合物的硅加成反应是一种重要的合成有机硅化合物的方法. 从不饱和化合物的种类出发, 主要涉及α,β-不饱和化合物、亚胺、Morita-Baylis-Hillman (MBH)醇类化合物、对苯醌甲基化合物、α,β-不饱和炔羰化合物以及α,β-不饱和砜类化合物, 综述了近几年在铜催化作用下这些不饱和化合物通过硅加成反应合成有机硅化合物的最新研究进展, 有利于加深对铜催化硅加成反应的理解.

关键词: 不饱和化合物, 铜催化, 硅加成, 有机硅化合物

Organosilicons are not only very useful functional molecules, but also important organic synthetic intermediates. It could be easily transformed into many other useful functional compounds under various conditions. So far, a lot of transition metal-catalyzed methods have been developed to prepare organosilicon compounds. Among them, copper-catalyzed silyl addition reactions to unsaturated compounds are extremely important for the synthesis of organosilicon compounds. Herein, the recent research progress in the synthesis of organosilicons by copper-catalyzed silyl addition of silyl reagents to diverse unsaturated compounds such as α,β-unsaturated carbonyl compounds, imines, Morita-Baylis-Hillman (MBH) alcohols, p-quinone methides, α,β-unsaturated alkyne carbonyl compounds and α,β-unsaturated sulfones is summarized. It will largely promote the development of such copper-catalyzed silyl addition reactions.

Key words: unsaturated compound, copper catalysis, silyl addition, organosilicon compound

引用此文

韩彪, 李维双, 陈舒晗, 张泽浪, 赵雪, 张瑶瑶, 朱磊. 铜催化不饱和化合物硅加成反应的研究进展[J]. 有机化学, 2023, 43(2): 555-572.

Biao Han, Weishuang Li, Shuhan Chen, Zelang Zhang, Xue Zhao, Yaoyao Zhang, Lei Zhu. Recent Advances in Copper-Catalyzed Silyl Addition of Unsaturated Compounds[J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 555-572.

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图/表 24

图式1. Cu(I)-NHC催化不饱和化合物不对称硅加成

Scheme 1. Cu(I)-NHC catalyzed asymmetric silyl addition of unsaturated compounds

图式2. Cu(I)-手性胺共催化α,β-不饱和醛不对称硅加成

Scheme 2. Cu(I)-chiral amine co-catalyzed asymmetric silyl addition of α,β-unsaturated aldehydes

图式3. Cu(I)催化不饱和酰胺和内酰胺不对称硅加成

Scheme 3. Cu(I) catalyzed asymmetric silyl addition of unsaturated lactams and amides

图式4. Cu(I)-NHC催化吲哚不对称硅加成

Scheme 4. Cu(I)-NHC catalyzed asymmetric silyl addition of indoles

图式5. Cu(I)-NHC催化合成手性α-氨基硅烷

Scheme 5. Cu(I)-NHC catalyzed synthesis of chiral α-amino silanes

图式6. Cu(II)催化α,β-不饱和化合物硅加成

Scheme 6. Cu(II)-catalyzed silyl addition of unsaturated compounds

图式7. Cu(II)非均相催化硅不对称加成

Scheme 7. Heterogeneous Cu(II)-catalyzed asymmetric silylation reaction

图式8. Cu(II)-廉价配体非均相催化硅加成

Scheme 8. Heterogeneous Cu(II)-cheap ligands catalyzed silyl addition reaction

图式9. 配体控制共轭二烯烃不饱和二酯区域选择性硅加成

Scheme 9. Ligand-controlled regioselective silyl addition reaction of conjugated diendioates

图式10. 铜催化共轭烯炔化合物区域选择性不对称硅加成

Scheme 10. Cu(II)-catalyzed regioselective asymmetric silyl addition reaction of conjugated enynes

图式11. 铜催化串联的不对称硅加成

Scheme 11. Copper-catalyzed tandem asymmetric silyl addition reactions

图式12. 铜催化亚胺的硅加成及可能的反应循环

Scheme 12. Copper-catalyzed silyl addition reactions of imines and proposed catalytic cycle

图式13. 铜催化亚胺的不对称硅加成

Scheme 13. Copper-catalyzed asymmetric silyl addition reactions of imines

图式14. 铜-氮杂卡宾催化亚胺的不对称硅加成

Scheme 14. Copper-NHC catalyzed asymmetric silyl addition reactions of imines

图式15. 手性α-氨基硅化合物的合成及转化

Scheme 15. Synthesis and transformation of chiral α-amino silicon compounds

图式16. 新型手性氮杂卡宾配体在亚胺硅加成中的应用

Scheme 16. Application of novel chiral azacarbene ligands in the silyl addition reactions of imines

图式17. 新型硅格氏试剂在硅加成反应中的应用

Scheme 17. Application of novel silicon Grignard reagents in the silyl addition reactions

图式18. Cu(I)-亚磷酰胺配体在亚胺不对称硅加成中的应用

Scheme 18. Application of Cu(I)-phosphoramidite ligands in asymmetric silyl addition reactions of imines

图式19. 配体在亚胺硅加成中控制立体选择性的应用

Scheme 19. Application of ligands in controlling stereoselectivity of the silyl addition of imines

图式20. Cu(II)催化的MBH化合物硅加成研究

Scheme 20. Cu(II)-catalyzed the silyl addition of MBH compounds

图式21. Cu(I)催化的对苯醌甲基化合物硅加成

Scheme 21. Cu(I)-catalyzed the silylation of p-quinone methides

图式22. Cu(II)催化的活化炔基的硅加成研究

Scheme 22. Cu(II)-catalyzed the silyl addition of activated alkynes

图式23. Cu(I)催化的烯炔化合物的硅加成研究

Scheme 23. Cu(I)-catalyzed the silyl addition of enynes

图式24. Cu(I)催化的α,β-不饱和砜的硅加成研究

Scheme 24. Cu(I)-catalyzed the silyl addition of α,β-unsaturated sulfones

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