Recent Advances in Copper-Catalyzed Silyl Addition of Unsaturated Compounds

doi:10.6023/cjoc202207043

Abstract

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

Cite this article

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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Fig. & Tab. 24

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

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

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

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

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

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

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

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

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

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

Scheme 11. Copper-catalyzed tandem asymmetric silyl addition reactions

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

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

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

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

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

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

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

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

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

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

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

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

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

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