Chemoselective heterogeneous iridium catalyzed hydrogenation of cinnamalaniline

Savela, Risto; Shcherban, Nataliya D.; Melander, Marko; Bezverkhyy, Igor; Simakova, Irina L.; Långvik, Otto; Kholkina, Ekaterina; Schindler, Tamara; Krauβ, Annabelle; Honkala, Karoliina; Murzin, Dmitry Yu.; Leino, Reko

doi:10.1039/d0cy01886d

Catal. Sci. Technol.

2021

DOI: 10.1039/d0cy01886d

|View full text |Cite

Chemoselective heterogeneous iridium catalyzed hydrogenation of cinnamalaniline

Risto Savela

Nataliya D. Shcherban

Marko Melander

et al.

Abstract: A selective atmospheric hydrogenation of unsaturated imines over heterogeneous iridium catalyst is described, in addition the selectivity is elucidated by DFT-calculations.

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2022

2025

Publication Types

Select...

Article3

Relationship

Self Cite0

Independent3

Authors

Journals

Cited by 3 publications

References 91 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

Computational insight into the selectivity of γ-valerolactone hydrodeoxygenation over Rh(111) and Ru(0001)

Kauppinen,

Słapa,

González Escobedo

et al. 2025

Surface Science

View full text Add to dashboard Cite

Computational insight into the selectivity of γ-valerolactone hydrodeoxygenation over Rh(111) and Ru(0001)

Kauppinen,

Słapa,

González Escobedo

et al. 2025

Surface Science

View full text Add to dashboard Cite

Understanding and Controlling Reactivity Patterns of Pd₁@C₃N₄-Catalyzed Suzuki–Miyaura Couplings

Usteri,

Giannakakis,

Bugaev

et al. 2024

ACS Catal.

View full text Add to dashboard Cite

Using heterogeneous single-atom catalysts (SACs) in the Suzuki−Miyaura coupling (SMC) has promising economic and environmental benefits over traditionally applied palladium complexes. However, limited mechanistic understanding hinders progress in their design and implementation. Our study provides critical insights into the working principles of Pd 1 @C 3 N 4 , a promising SAC for the SMC. We demonstrate that the base, ligand, and solvent play pivotal roles in facilitating interface formation with reaction media, activating Pd centers, and modulating competing reaction pathways. Controlling the previously overlooked interplay between base strength, reagent solubility, and surface wetting is essential for mitigating mass transfer limitations in the triphasic reaction system and promoting catalyst reusability. Optimum conditions for Pd 1 @C 3 N 4 require polar solvents, intermediate base strength, and increased water content. Our investigations reveal that high selectivity requires minimizing competitive coordination of bases and phosphine ligands to the Pd centers, to avoid homocoupling and alternative reductive elimination mechanisms giving rise to phosphonium side-products. Furthermore, in situ XAS investigations probing electronic structures and coordination environments of Pd sites further rationalize the base and ligand coordination, confirming and expanding upon previous computational hypotheses for Pd 1 @C 3 N 4 . This understanding allows for designing a more selective ligand-free reaction pathway using the solvent and base to modulate the chemical environment of the active sites. We highlight the importance of environment-compatible surface tension, the creation of coordinatively available active sites, and the stabilization of partially reduced Pd centers, emphasizing the importance of mechanistic studies to advance the design of SACs in organic liquid phase reactions.

show abstract

Iridium supported on porous polypyridine-oxadiazole as high-activity and recyclable catalyst for the borrowing hydrogen reaction

Mao

Yao

et al. 2022

Green Chem.

View full text Add to dashboard Cite

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.

Chemoselective heterogeneous iridium catalyzed hydrogenation of cinnamalaniline

Abstract: A selective atmospheric hydrogenation of unsaturated imines over heterogeneous iridium catalyst is described, in addition the selectivity is elucidated by DFT-calculations.

Cited by 3 publications

References 91 publications

Computational insight into the selectivity of γ-valerolactone hydrodeoxygenation over Rh(111) and Ru(0001)

Computational insight into the selectivity of γ-valerolactone hydrodeoxygenation over Rh(111) and Ru(0001)

Understanding and Controlling Reactivity Patterns of Pd₁@C₃N₄-Catalyzed Suzuki–Miyaura Couplings

Iridium supported on porous polypyridine-oxadiazole as high-activity and recyclable catalyst for the borrowing hydrogen reaction

Contact Info

Product

Resources

About

Chemoselective heterogeneous iridium catalyzed hydrogenation of cinnamalaniline

Abstract: A selective atmospheric hydrogenation of unsaturated imines over heterogeneous iridium catalyst is described, in addition the selectivity is elucidated by DFT-calculations.

Cited by 3 publications

References 91 publications

Computational insight into the selectivity of γ-valerolactone hydrodeoxygenation over Rh(111) and Ru(0001)

Computational insight into the selectivity of γ-valerolactone hydrodeoxygenation over Rh(111) and Ru(0001)

Understanding and Controlling Reactivity Patterns of Pd1@C3N4-Catalyzed Suzuki–Miyaura Couplings

Iridium supported on porous polypyridine-oxadiazole as high-activity and recyclable catalyst for the borrowing hydrogen reaction

Contact Info

Product

Resources

About

Understanding and Controlling Reactivity Patterns of Pd₁@C₃N₄-Catalyzed Suzuki–Miyaura Couplings