Recent Advances in Transition Metal-Catalyzed C—Si Bond Cleavage of Silacyclobutanes

doi:10.6023/cjoc202306019

Abstract

Due to the widespread application of various organosilicon compounds in material science, electronic devices and pharmaceutical research, it is of great significance to develop green and efficient synthetic methods for diverse silicon-con- taining molecules. Silacyclobutane is an important kind of small-membered rings, which exhibits unique reactivities under transition metal catalysis to cleave the C—Si bond driven by the inherent ring strain and Lewis acidity. The resulting Si—M species can then be transformed into various organosilicon compounds. Herein, the recent advances of Pd, Rh, and Ni-catalyzed C—Si bond cleavage reactions of silacyclobutanes are summarized in detail, and the mechanism and development tendency of such reactions are briefly discussed.

Key words: transition metal catalysis, silacyclobutane, C—Si bond cleavage

Cite this article

Min Liu, Liping Qi, Dongbing Zhao. Recent Advances in Transition Metal-Catalyzed C—Si Bond Cleavage of Silacyclobutanes[J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3508-3525.

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Fig. & Tab. 38

Figure 1. Examples of silicon-containing molecules of medicinal interest

Scheme 1. Transition metal catalyzed C—Si bond cleavage of silacyclobutanes

Scheme 2. Pd-catalyzed ring expansion reaction of silacyclobutanes with electron deficient alkynes

Scheme 4. Pd-catalyzed a asymmetric intramolecular ring expansion reaction of silacyclobutanes with alkynes

Scheme 5. Pd-catalyzed asymmetric intermolecular ring expansion reaction of silacyclobutanes with alkynes

Scheme 6. Pd-catalyzed ring expansion reaction of polysubstituted silacyclobutanes with alkynes

Scheme 7. Rh-catalyzed intermolecular ring expansion reaction of silacyclobutanes with terminal alkynes

Scheme 8. Asymmetric total synthesis of (-)-sila-mesembranol

Scheme 9. Rh-catalyzed asymmetric dual ring expansion of spirosilabicyclobutanes with alkynes

Scheme 10. Rh-catalyzed asymmetric ring expansion of 4/5- spirosilafluorenes with alkynes

Scheme 11. Rh-catalyzed ring expansion reaction of silacyclobutanes with unsymmetrical activated alkynes

Scheme 12. Ni-catalyzed divergent reactions of silacyclobutanes with alkynes

Scheme 13. Pd-catalyzed intermolecular ring expansion reaction of silacyclobutanes with cyclopropenes

Scheme 14. Pd-catalyzed intermolecular ring expansion reaction of silacyclobutanes with allenoates

Scheme 15. Ni-catalyzed ring expansion reaction of benzosilacyclobutanes with ethyl cyclopropylideneacetate

Scheme 16. Pd-catalyzed intermolecular ring expansion reaction of silacyclobutanes with enones

Scheme 17. Ni-catalyzed ring expansion reaction of (benzo)- silacyclobutanes with aldehydes

Scheme 18. Ni-catalyzed asymmetrical ring expansion reaction of silacyclobutanes with aldehydes

Scheme 19. Ni-catalyzed ring expansion reaction of (benzo)silacyclobutanes with acylsilanes

Scheme 20. Ni-catalyzed site- and regio-selective incorporation of CO2 into the benzosilacyclobutenes

Scheme 21. Pd-catalyzed intermolecular ring expansion reaction of silacyclobutanes with carbenes

Scheme 22. Pd-catalyzed intermolecular ring expansion reaction of benzosilacyclobutanes with carbenes

Scheme 23. Pd-catalyzed ring expansion reaction of silacyclobutanes with acyl chlorides

Scheme 24. Pd-catalyzed three-component reaction of silacyclobutanes with organic halides and CO

Scheme 25. Pd-catalyzed ring expansion reaction of silacyclobutanes with acid anhydrides

Scheme 26. Pd-catalyzed Hiyama-Denmark coupling reaction of silacyclobutanes

Scheme 27. Pd-catalyzed cross dimerization of (benzo)silacy- clobutanes with (benzo)cyclobutanes

Scheme 28. Pd-catalyzed cross dimerization of (benzo)silacy- clobutanes with cycolpropenones or biphenylenes

Scheme 29. Pd-catalyzed [4＋4] cycloaddition of silacyclobutanes with 2-iodobiphenyls

Scheme 30. Ni-catalyzed enantioselective ring opening reaction of silacyclobutanes with alkynes

Scheme 31. Ni-catalyzed silylation of alkenes with silacyclobutanes

Scheme 32. Ni-catalyzed intramolecular ring expansion reaction of silacyclobutanes with alkenes

Scheme 33. Rh-catalyzed intramolecular silylation between C—H bond and silacyclobutanes

Scheme 34. Rh-catalyzed asymmetric intramolecular C—H silylation of silacyclobutanes

Scheme 35. Rh-catalyzed C—H bond enantioselective silylation

Scheme 36. Rh-catalyzed silylation of C(sp)—H bond

Scheme 37. Ni-catalyzed hydrogen transfer reaction of silacyclobutanes with hydrosilanes

Scheme 38. Ni-catalyzed ring open reaction of silacyclobutanes with aryl iodides

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