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

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Cited by 6 publications

References 36 publications

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Nucleophilic Addition and Substitution Reactions In‐Water

Devi,

Rinu,

Anilkumar

2024

Organic Transformations in Water

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Nucleophilic Addition and Substitution Reactions In‐Water

Devi,

Rinu,

Anilkumar

2024

Organic Transformations in Water

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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

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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.

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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

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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.

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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 6 publications

References 36 publications

Nucleophilic Addition and Substitution Reactions In‐Water

Nucleophilic Addition and Substitution Reactions In‐Water

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

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