Multi-site programmable functionalization of alkenes via controllable alkene isomerization

Wu, Zhengliang; Meng, Jingjie; Liu, Huikang; Li, Yunyi; Zhang, Xiao; Zhang, Wanbin

doi:10.1038/s41557-023-01209-x

Nat. Chem.

2023

DOI: 10.1038/s41557-023-01209-x

|View full text |Cite

Multi-site programmable functionalization of alkenes via controllable alkene isomerization

Zhengliang Wu

Jingjie Meng

Huikang Liu

et al.

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2023

2024

Publication Types

Select...

Article6

Relationship

Self Cite2

Independent4

Authors

Journals

Cited by 22 publications

(1 citation statement)

References 48 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Thus, selective functionalization of alkenes is a powerful method to increase their molecular complexity . Compared with 1,2-difunctionalization of alkenes, 1,3-difunctionalization of alkenes is difficult to achieve , because the transfer of the reaction site requires an additional β-H elimination process in transition-metal-catalyzed reactions. The β-H elimination, as shown in Scheme a, produces monofunctionalized byproducts unless a catalyst is capable of migratory insertion.…”

mentioning

confidence: 99%

1,3-Difunctionalization of Alkenes by Cobaloxime Photocatalysis

Yu,

Cheng,

Zeng

et al. 2024

Org. Lett.

View full text Add to dashboard Cite

Represented herein is the first 1,3-difunctionalization of alkenes via photocatalysis. A single cobaloxime is used to carry out two catalytic cycles in which cobaloxime is used not only as a photocatalyst to initiate the reaction but also as a metal catalyst for the β-H elimination process. Electron-deficient alkenes, electron-rich alkenes, and unactivated alkenes could be directly converted to 1,3bisphosphorylated products, even unsymmetric 1,3-bisphosphorylated products, with only H 2 as a byproduct under extremely mild reaction conditions.

show abstract

mentioning

confidence: 99%

1,3-Difunctionalization of Alkenes by Cobaloxime Photocatalysis

Yu,

Cheng,

Zeng

et al. 2024

Org. Lett.

View full text Add to dashboard Cite

show abstract

Advancing Heterogeneous Organic Synthesis With Coordination Chemistry‐Empowered Single‐Atom Catalysts

Ye,

Li,

Zhang

et al. 2024

Advanced Materials

View full text Add to dashboard Cite

For traditional metal complexes, intricate chemistry is required to acquire appropriate ligands for controlling the electron and steric hindrance of metal active centers. Comparatively, the preparation of single‐atom catalysts is much easier with more straightforward and effective accesses for the arrangement and control of metal active centers. The presence of coordination atoms or neighboring functional atoms on the supports' surface ensures the stability of metal single‐atoms and their interactions with individual metal atoms substantially regulate the performance of metal active centers. Therefore, the collaborative interaction between metal and the surrounding coordination environment enhances the initiation of reaction substrates and the formation and transformation of crucial intermediate compounds, which imparts single‐atom catalysts with significant catalytic efficacy, rendering them a valuable framework for investigating the correlation between structure and activity, as well as the reaction mechanism of catalysts in organic reactions. Herein, comprehensive overviews of the coordination interaction for both homogeneous metal complexes and single‐atom catalysts in organic reactions are provided. Additionally, reflective conjectures about the advancement of single‐atom catalysts in organic synthesis are also proposed to present as a reference for later development.

show abstract

Iridium‐Catalyzed Remote Site‐Switchable Hydroarylation of Alkenes Controlled by Ligands

Li,

Luo,

Ren

et al. 2023

Angewandte Chemie

Self Cite

View full text Add to dashboard Cite

An iridium‐catalyzed remote site‐switchable hydroarylation of alkenes was reported, delivering the products functionalized at the subterminal methylene and terminal methyl positions on an alkyl chain controlled by two different ligands, respectively, in good yields and with good to excellent site‐selectivities. The catalytic system showed good functional group tolerance and a broad substrate scope, including unactivated and activated alkenes. More importantly, the regioconvergent transformations of mixtures of isomeric alkenes were also successfully realized. The results of the mechanistic studies demonstrate that the reaction undergoes a chain‐walking process to give an [Ar‐Ir‐H] complex of terminal alkene. The subsequent processes proceed through the modified Chalk−Harrod‐type mechanism via the migratory insertion of terminal alkene into the Ir−C bond followed by C−H reductive elimination to afford the hydrofunctionalization products site‐selectively.

show abstract

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

customersupport@researchsolutions.com

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

Multi-site programmable functionalization of alkenes via controllable alkene isomerization

Cited by 22 publications

References 48 publications

1,3-Difunctionalization of Alkenes by Cobaloxime Photocatalysis

1,3-Difunctionalization of Alkenes by Cobaloxime Photocatalysis

Advancing Heterogeneous Organic Synthesis With Coordination Chemistry‐Empowered Single‐Atom Catalysts

Iridium‐Catalyzed Remote Site‐Switchable Hydroarylation of Alkenes Controlled by Ligands

Contact Info

Product

Resources

About