Dehydrative amination of benzhydrols with electron-withdrawing group-substituted 2-aminopyridines utilizing Au(<scp>iii</scp>)/TPPMS catalyst system in water

Hikawa, Hidemasa; Nakayama, Taku; Nakamura, Shunki; Kikkawa, Shoko; Azumaya, Isao

doi:10.1039/d2ob00673a

Org. Biomol. Chem.

2022

DOI: 10.1039/d2ob00673a

|View full text |Cite

Dehydrative amination of benzhydrols with electron-withdrawing group-substituted 2-aminopyridines utilizing Au(iii)/TPPMS catalyst system in water

Hidemasa Hikawa

Taku Nakayama

Shunki Nakamura

et al.

Abstract: We report a method for gold(III)/TPPMS-catalyzed direct amination of benzhydrols using 2-aminopyridines with poor nucleophilic character in water. Various functional groups such as electron-withdrawing nitro, cyano and halogen groups were...

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...

Article5

Relationship

Self Cite0

Independent5

Authors

Journals

Cited by 5 publications

References 36 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

Fabricating Effective and Recyclable Cadmium‐based Coordination Polymer for Selective Synthesis of 1,5‐Benzodiazepines

Chen,

Li,

Wang

et al. 2023

Asian J Org Chem

View full text Add to dashboard Cite

Metal coordination polymers are widely applied in the synthesis of heterocyclic compounds due to the advantages of highly dispersed metal active sites, low cost and strong designability. Herein, employing the 9‐benzyl‐3,6‐di(1H‐pyrazol‐1‐yl)‐9H‐carbazole (BPC) as a ligand, the cadmium‐coordinated polymer compound (Cd‐BPC) was facilely prepared by solvothermal method and characterized by energy dispersive spectrometer (EDS), flourier‐transform infrared spectroscopy (FT‐IR), scanning electron microscope (SEM), transmission electron microscopy (TEM) and X‐ray photoelectron spectrometry (XPS). Employing the Cd‐BPC polymer as a catalyst, 1,5‐benzodiazepine derivatives were produced with relatively high yields through the reaction of o‐phenylenediamine with ketones, and o‐phenylenediamine with alcohols. Additionally, Cd‐BPC could be reused for at least 5 times without significant decrease.

show abstract

Fabricating Effective and Recyclable Cadmium‐based Coordination Polymer for Selective Synthesis of 1,5‐Benzodiazepines

Chen,

Li,

Wang

et al. 2023

Asian J Org Chem

View full text Add to dashboard Cite

show abstract

Pd(0)/TPPMS‐Catalyzed Tsuji–Trost Type Cross‐Coupling of Allylic Alcohols with Organoboron Compounds in Water

Hikawa,

Fu,

Nakayama

et al. 2024

Asian J Org Chem

View full text Add to dashboard Cite

We demonstrated that the combination of a Pd(0) catalyst and a water‐soluble TPPMS ligand has high activity for the direct arylation of readily available allylic alcohols in the Tsuji‐Trost type cross‐coupling. Various organoboron reagents can be applied, enabling rapid access to the corresponding arylated products with a wide range of functional group tolerance. Kinetic studies revealed a first‐order rate dependence for the allylic alcohol, boronic acid, CsF and Pd(0)/TPPMS concentrations. A Hammett study found a slightly positive r value of 0.79, suggesting that a partial negative charge is generated on the aromatic ring of the aryl boronate in the rate‐determining transmetalation step. Based on several control experiments, we concluded that the transmetalation employing CsF would proceed via the oxo‐palladium mechanism.

show abstract

Pyrazolyl-pyrimidine porous-organic-polymer supported single-site nickel composites as efficient catalysts for the synthesis of substituted pyrimidines

Li,

Zeng,

Wang

et al. 2023

Chemical Engineering Journal

View full text Add to dashboard Cite

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

hi@scite.ai

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

Henderson, NV 89052, USA

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.

Dehydrative amination of benzhydrols with electron-withdrawing group-substituted 2-aminopyridines utilizing Au(iii)/TPPMS catalyst system in water

Abstract: We report a method for gold(III)/TPPMS-catalyzed direct amination of benzhydrols using 2-aminopyridines with poor nucleophilic character in water. Various functional groups such as electron-withdrawing nitro, cyano and halogen groups were...

Cited by 5 publications

References 36 publications

Fabricating Effective and Recyclable Cadmium‐based Coordination Polymer for Selective Synthesis of 1,5‐Benzodiazepines

Fabricating Effective and Recyclable Cadmium‐based Coordination Polymer for Selective Synthesis of 1,5‐Benzodiazepines

Pd(0)/TPPMS‐Catalyzed Tsuji–Trost Type Cross‐Coupling of Allylic Alcohols with Organoboron Compounds in Water

Pyrazolyl-pyrimidine porous-organic-polymer supported single-site nickel composites as efficient catalysts for the synthesis of substituted pyrimidines

Contact Info

Product

Resources

About