Palladium-catalyzed three-component synthesis of phosphine-containing tetrasubstituted acyclic unsymmetric all-carbon olefins

Ma, Xingxing; Li, Puhui; Liang, Jinchao; An, Hejun; Yang, Kai; Song, Qiuling

doi:10.1016/j.xcrp.2021.100629

Cited by 6 publications

(3 citation statements)

References 53 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Polysubstituted olefins are essential functional groups that serve as the building blocks for a diverse array of materials and bioactive molecules. [1][2][3] They possess remarkable versatility as starting materials in the synthesis of various compounds, including those utilized in pharmaceuticals and materials science. Moreover, they are prevalent in numerous natural products.…”

Section: Introductionmentioning

confidence: 99%

“…The double bond of alkenes, characterized by electron density and high energy, imparts distinctive properties, making them pivotal for a multitude of organic transformations. [1][2][3][4][5] However, achieving the synthesis of alkenes with diverse (all-carbon) multisubstituents through stereodefined methods i.e. when aiming for Z/E stereoselectivity control, often demands the development of intricate synthetic routes.…”

Section: Introductionmentioning

confidence: 99%

“…when aiming for Z/E stereoselectivity control, often demands the development of intricate synthetic routes. [1][2][3][4] Classical double bond-forming methods such as the Wittig and Horner-Wadsworth-Emmons reactions encounter serious problems of generality and stereoselectivity when used to form polysubstituted double bonds. 4,6 Consequently, alternative approaches have been devised to synthesize geometrically defined polysubstituted olefins.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Stereoselective C−B and C−H Bonds Functionalization of polyBorylated Alkenes

Vaishanv,

Eghbarieh,

Jagtap

et al. 2023

Preprint

View full text Add to dashboard Cite

Alkenes are fundamental functional groups which feature in various materials and bioactive molecules; however, efficient divergent strategies for their stereodefined synthesis are difficult. In this regard, numerous synthetic methodologies have been developed to construct carbon–carbon bonds with regio- and stereoselectivity, enabling the predictable and efficient synthesis of stereodefined alkenes. In fact, an appealing alternative approach for accessing challenging stereodefined alkenes molecular frameworks could involve the sequential selective activation and cross-coupling of strong bonds instead of conventional C–C bond formation. In this study, we introduce a programmed site- and stereoselective strategies that capitalizes on the versatile reactivity of readily accessible polymetalloid alkenes, through a tandem cross-coupling reaction, which is catalyzed by an organometallic Rh-complex to produce complex molecular scaffolds. By merging selective C–B and remote C–H bond functionalization, we achieve the generation of polyfunctional C(sp2)-nucleophilic species intermediates. These species can be further modified by selective coupling reactions with various C-based electrophiles, enabling the formation of C(sp2)–C(sp3) bond for the generation of even more complex molecular architectures using the readily available starting polyborylated-alkenes.

show abstract

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Stereoselective C−B and C−H Bonds Functionalization of polyBorylated Alkenes

Vaishanv,

Eghbarieh,

Jagtap

et al. 2023

Preprint

View full text Add to dashboard Cite

show abstract

Stereoselective C−B and C−H Bonds Functionalization of PolyBorylated Alkenes

Vaishanv,

Eghbarieh,

Jagtap

et al. 2024

Angewandte Chemie

View full text Add to dashboard Cite

Alkenes are fundamental functional groups which feature in various materials and bioactive molecules; however, efficient divergent strategies for their stereodefined synthesis are difficult. In this regard, numerous synthetic methodologies have been developed to construct carbon–carbon bonds with regio‐ and stereoselectivity, enabling the predictable and efficient synthesis of stereodefined alkenes. In fact, an appealing alternative approach for accessing challenging stereodefined alkenes molecular frameworks could involve the sequential selective activation and cross‐coupling of strong bonds instead of conventional C–C bond formation. In this study, we introduce a series of programmed site‐ and stereoselective strategies that capitalizes on the versatile reactivity of readily accessible polymetalloid alkenes (i.e. polyborylated alkenes), through a tandem cross‐coupling reaction, which is catalyzed by an organometallic Rh‐complex to produce complex molecular scaffolds. By merging selective C–B and remote C–H bond functionalization, we achieve the in‐situ generation of polyfunctional C(sp2)‐nucleophilic intermediates. These species can be further modified by selective coupling reactions with various C‐based electrophiles, enabling the formation of C(sp2)–C(sp3) bond for the generation of even more complex molecular architectures using the readily available starting polyborylated‐alkenes. Mechanistic and computational studies have provided insight into the origins of the stereoselectivities and C–H activation via a 1,4‐Rh migration process.

show abstract

Stereoselective C−B and C−H Bonds Functionalization of PolyBorylated Alkenes

Vaishanv,

Eghbarieh,

Jagtap

et al. 2024

Angew Chem Int Ed

View full text Add to dashboard Cite

Alkenes are fundamental functional groups which feature in various materials and bioactive molecules; however, efficient divergent strategies for their stereodefined synthesis are difficult. In this regard, numerous synthetic methodologies have been developed to construct carbon–carbon bonds with regio‐ and stereoselectivity, enabling the predictable and efficient synthesis of stereodefined alkenes. In fact, an appealing alternative approach for accessing challenging stereodefined alkenes molecular frameworks could involve the sequential selective activation and cross‐coupling of strong bonds instead of conventional C–C bond formation. In this study, we introduce a series of programmed site‐ and stereoselective strategies that capitalizes on the versatile reactivity of readily accessible polymetalloid alkenes (i.e. polyborylated alkenes), through a tandem cross‐coupling reaction, which is catalyzed by an organometallic Rh‐complex to produce complex molecular scaffolds. By merging selective C–B and remote C–H bond functionalization, we achieve the in‐situ generation of polyfunctional C(sp2)‐nucleophilic intermediates. These species can be further modified by selective coupling reactions with various C‐based electrophiles, enabling the formation of C(sp2)–C(sp3) bond for the generation of even more complex molecular architectures using the readily available starting polyborylated‐alkenes. Mechanistic and computational studies have provided insight into the origins of the stereoselectivities and C–H activation via a 1,4‐Rh migration process.

show abstract

Palladium-catalyzed three-component synthesis of phosphine-containing tetrasubstituted acyclic unsymmetric all-carbon olefins

Cited by 6 publications

References 53 publications

Stereoselective C−B and C−H Bonds Functionalization of polyBorylated Alkenes

Stereoselective C−B and C−H Bonds Functionalization of polyBorylated Alkenes

Stereoselective C−B and C−H Bonds Functionalization of PolyBorylated Alkenes

Stereoselective C−B and C−H Bonds Functionalization of PolyBorylated Alkenes

Contact Info

Product

Resources

About