Development of P, S and Si-Stereogenic Compounds Synthesis via Palladium Catalysis

doi:10.6023/cjoc202208043

Abstract

Compounds bearing phosphorus, sulfur or silicon stereogenic center have a wide range of applications in the fields of medicine, pesticides, organic synthesis and material science. Efficient construction of these three types of heteroatom-centered chirality has gradually developed as one of the most important frontiers in asymmetric synthetic chemistry. This paper focuses on the recent development of the asymmetric synthesis via palladium/chiral complexes or using the chiral auxiliaries. Strategies such as P—X (X=H, Si or O) bond activation, desymmetrization, and cycloaddition for P-chiral compounds synthesis are introduced, while the methods for S and Si chiral compounds are somewhat similar. The mechanism of some representative examples and their potential applications are also included.

Key words: palladium catalysis, P-chirality, S-chirality, Si-chirality, asymmetric catalysis

Cite this article

Jieming Zhang, Hang Ni, Qi Wu, Junfeng Yang, Junliang Zhang. Development of P, S and Si-Stereogenic Compounds Synthesis via Palladium Catalysis[J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3118-3128.

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Fig. & Tab. 25

Scheme 1. Pd-catalyzed asymmetric P—H functionalization

Scheme 2. Proposed mechanism of the enantioselectivity enrichment of the racemic P-H compound

Scheme 3. Mechanistic study of DKR of P-H compounds

Scheme 4. DKR of racemic P-H compounds

Scheme 5. Pd-catalyzed DKR of SPO

Scheme 6. Pd/DuPhos-catalyzed asymmetric hydrophosphination of alkynes

Scheme 7. Pd/XiaoPhos-catalyzed asymmetric hydrophosphination of alkynes

Scheme 8. Pd-catalyzed asymmetric P-Si coulpling

Scheme 9. Pd-catalyzed C—P bond metathesis

Scheme 10. Pd-catalyzed chirality transfer reaction of phosphoramidites

Scheme 11. Pd-Catalyzed stereospecific C—P coupling

Scheme 12. Pd-catalyzed desymmetrization of P-stereogenic compounds

Scheme 13. Pd-catalyzed asymmetric cycloaddition of P-stereogenic compounds

Scheme 14. Pd/Josiphos-catalyzed asymmetric arylation of sulfenate anions

Scheme 15. Pd/PCphos-catalyzed asymmetric arylation of sulfenate anions

Scheme 16. Pd-catalyzed asymmetric olefination of sulfenate anions

Scheme 17. Pd-catalyzed asymmetric C—H olefination of diaryl sulfoxides through parallel kinetic resolution and desymmetrization

Scheme 18. Pd-catalyzed kinetic resolution of S-stereogenic imines

Scheme 19. Pd-catalyzed desymmetrization of silacyclobutanes

Scheme 20. Pd-catalyzed intermolecular desymmetrization of silacyclobutanes

Scheme 21. Proposed mechanism of Pd-catalyzed desymmetrization of silacyclobutanes with alkynes to silicon-stereogenic silanes based on a density functional theory study

Scheme 22. Pd-catalyzed desymmetration of Si-stereogenic dibenzosiloes

Scheme 23. Pd-catalyzed aymmetric arylation of silane

Scheme 24. Study of ligand structure for Pd-catalyzed asymmetric arylation of silane

Scheme 25. Pd-catalyzed desymmetrization of silanes

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