Construction of Silicon-Stereogenic Center via Catalytic Asymmetric Si—H/X—H Dehydrogenative Coupling

doi:10.6023/cjoc202305001

Abstract

Owing to its unique structure and properties, silicon-stereogenic silanes have displayed valuable application prospects in the fields of organic synthesis, functional materials and biomedicine, and have received extensive attention from chemists. In recent years, methods for the construction of silicon-stereogenic center have been rapidly developed, especially the use of transition metal catalysis to conduct the desymmetrization of prochiral silanes. Among them, asymmetric catalytic Si—H/X—H dehydrogenative coupling (Si-CADC) using dihydrosilane as the substrate has become an important approach and key technology for the construction of silicon-stereogenic center, because of its advantages of high efficiency, high atomic economy, good structural diversity and high enantioselectivity. According to the different reaction categorie and products, this review will mainly summarize and discuss in three stages: (1) asymmetric dehydrogenative coupling tandem strategy to construct tetrasubstituted silicon-stereogenic silanes, (2) intramolecular Si—H/C—H dehydrogenative coupling to construct cyclic silicon-stereogenic monohydrosilanes, and (3) intermolecular Si—H/X—H dehydrogenative coupling to construct a variety of ayclic silicon-stereogenic silanes.

Key words: silicon-stereogenic chirality, organosilicon chemistry, dihydrosilane, asymmetric catalysis, dehydrogenative coupling

Cite this article

Jiayi Zhao, Yicong Ge, Chuan He. Construction of Silicon-Stereogenic Center via Catalytic Asymmetric Si—H/X—H Dehydrogenative Coupling[J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3352-3366.

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Fig. & Tab. 21

Figure 1. Si-stereogenic functional molecules

Scheme 1. Challenges to access Si-stereogenic center

Scheme 2. Methods to access Si-stereogenic center

Scheme 3. Catalytic asymmetric Si—H/X—H dehydrogenative coupling

Scheme 4. Intramolecular asymmetric double dehydrogenative coupling for the construction of axially chiral spirosilabifluorene

Scheme 5. Design of tandem strategy for the construction of Si-stereogenic center via asymmetric dehydrogenative coupling

Scheme 6. Construction of Si-stereogenic silanes by tandem asymmetric dehydrogenative coupling/alkene hydrosilylation

Scheme 7. Mechanism of Rh-catalyzed tandem asymmetric dehydrogenative coupling/alkene hydrosilylation

Scheme 8. Tandem asymmetric Si—H/C(sp3)—H dehydrogenative coupling/alkene hydrosilylation

Scheme 9. Asymmetric dehydrogenative coupling for the construction of Si-stereogenic monohydrosilanes

Scheme 10. Asymmetric dehydrogenative coupling for the construction of six- and seven-membered Si-stereogenic heterocycles

Scheme 11. Asymmetric Si—H/C(sp3)—H dehydrogenative coupling for the construction of axial and Si-stereogenic chiralities

Scheme 12. Intermolecular asymmetric Si—H/C—H dehydrogenative coupling

Scheme 13. Asymmetric Si—H/C—H dehydrogenative coupling of dihydrosilanes with thiophenes

Scheme 14. Early examples of asymmetric Si—H/O—H dehydrogenative coupling

Scheme 15. Asymmetric Si—H/O—H dehydrogenative coupling for the construction of Si-stereogenic siloxanes

Scheme 16. Catalytic asymmetric hydrolytic oxidation of dihydrosilanes for the construction of chiral silanols

Scheme 17. Mechanistic study of the asymmetric hydrolytic oxidation

Scheme 18. Copper-catalyzed asymmetric hydrolytic oxidation of dihydrosilanes

Scheme 19. Copper-catalyzed asymmetric dehydrogenative coupling of silanediols for the construction of chiral silanols

Scheme 20. Asymmetric Si—H/N—H dehydrogenative coupling for the construction of Si-stereogenic silazanes

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不对称催化Si—H/X—H脱氢偶联构筑硅中心手性