A Detailed Dft Theoretical Investigation of the Mechanism of Quinoline Hydrogenation Catalyzed by a (1,5-Cyclooctadiene)Rhodium(I) Complex DOI
Merlín Rosales,

Federico Arrieta,

Pablo J. Baricelli

и другие.

Опубликована: Янв. 1, 2024

A detailed catalytic cycle for the hydrogenation of quinoline (Q) to 1,2,3,4-tetrahydroquinoline (THQ) catalyzed by a cationic rhodium complex containing 1,5-cyclooctadiene (COD) ligand was computationally investigated using DFT. It found that catalytically active species [Rh(COD)(kN-Q)]+ and addition each two dihydrogen molecules occurs through initial coordination forming h2-H2 intermediates, followed subsequent hydride transfer Q DHQ ligands (migratory insertion reductive elimination, respectively). Except elimination THQ product, all elementary steps were reversible, which is an important point in connection with hydrogen storage models. Our theoretical DFT calculations are consistent experimental results previously reported.

Язык: Английский

Transfer Hydrogenation of N- and O-Containing Heterocycles Including Pyridines with H3N–BH3 Under the Catalysis of the Homogeneous Ruthenium Precatalyst DOI
Tarun Kumar Bhatt, Kishore Natte

Organic Letters, Год журнала: 2024, Номер 26(4), С. 866 - 871

Опубликована: Янв. 25, 2024

In this study, we report a transfer hydrogenation protocol that utilizes borane–ammonia (H3N–BH3) as the hydrogen source and commercially available RuCl3·xH2O precatalyst for selective aromatic reduction of quinolines, quinoxalines, pyridines, pyrazines, indoles, benzofurans, furan derivatives to form corresponding alicyclic heterocycles in good excellent isolated yields. Applications straightforward include efficient preparation useful key pharmaceutical intermediates, such donepezil flumequine, including biologically active compound.

Язык: Английский

Процитировано

9
Co(II)-Catalyzed Additive-Free Transfer Hydrogenation of N-Heteroarenes at Room Temperature DOI

Divya Mahapatra,

Anirban Sau,

Tanmoy Kumar Ghosh

и другие.

Organic Letters, Год журнала: 2024, Номер 26(28), С. 6001 - 6005

Опубликована: Июль 8, 2024

Traditional catalyst development relies on multistep synthesis and isolation of ligand precatalyst. Designing a catalytic system that can be assembled

Язык: Английский

Процитировано

6
Aqueous-biphasic catalysis: A technological alternative for the use of organometallic complexes in hydrogenation and hydroformylation reactions with possible industrial application DOI
Pablo J. Baricelli, Juan Pereira, Merlín Rosales

и другие.

Catalysis Today, Год журнала: 2024, Номер 443, С. 114969 - 114969

Опубликована: Авг. 6, 2024

Язык: Английский

Процитировано

6
Manganese catalysed reduction of nitriles with amine boranes DOI Creative Commons
Stefan Weber, Ines Blaha, Karl Kirchner

и другие.

Catalysis Science & Technology, Год журнала: 2024, Номер 14(17), С. 4843 - 4847

Опубликована: Янв. 1, 2024

The room temperature reduction of various nitriles using amine boranes catalysed by a manganese( i ) alkyl complex is described. Based on experimental findings, plausible mechanistic scenario presented.

Язык: Английский

Процитировано

5
Manganese-catalyzed asymmetric transfer hydrogenation of quinolines in water using ammonia borane as a hydrogen source DOI
Wenhao Mao, Dingguo Song,

Jiyuan Guo

и другие.

Green Chemistry, Год журнала: 2024, Номер 26(10), С. 5933 - 5939

Опубликована: Янв. 1, 2024

The first example of manganese-catalyzed asymmetric transfer hydrogenation N-heteroaromatics in water with good yields and ee up to 99%.

Язык: Английский

Процитировано

4
Base Promoted Hydrogenation of N-Heteroarenes with Ammonia Borane and DMSO DOI
Dongxu Jia, Zhenkang Ai,

Xinya Yuan

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Апрель 10, 2025

Herein, we report a sodium tert-butoxide-promoted reduction of N-heteroarenes using ammonia borane and dimethyl sulfoxide (DMSO) under mild reaction conditions. This method demonstrates broad functional group compatibility across diverse N-heteroarene substrates. Notably, substituting DMSO with deuterated DMSO-d6 enables the synthesis C3-deuterated 1,2,3,4-tetrahydroquinolines remarkable positional selectivity. Mechanistic investigations indicate that protons are derived from both DMSO. strategy establishes novel environmentally benign approach for (deuterated) N-heterocycles, offering practical advantages in terms operational simplicity sustainable

Язык: Английский

Процитировано

0
A detailed DFT theoretical investigation of the mechanism of quinoline hydrogenation catalyzed by a (1,5-cyclooctadiene)rhodium(I) complex DOI
Merlín Rosales,

Federico Arrieta,

Pablo J. Baricelli

и другие.

Catalysis Today, Год журнала: 2024, Номер unknown, С. 115160 - 115160

Опубликована: Дек. 1, 2024

Язык: Английский

Процитировано

2
A Detailed Dft Theoretical Investigation of the Mechanism of Quinoline Hydrogenation Catalyzed by a (1,5-Cyclooctadiene)Rhodium(I) Complex DOI
Merlín Rosales,

Federico Arrieta,

Pablo J. Baricelli

и другие.

Опубликована: Янв. 1, 2024

A detailed catalytic cycle for the hydrogenation of quinoline (Q) to 1,2,3,4-tetrahydroquinoline (THQ) catalyzed by a cationic rhodium complex containing 1,5-cyclooctadiene (COD) ligand was computationally investigated using DFT. It found that catalytically active species [Rh(COD)(kN-Q)]+ and addition each two dihydrogen molecules occurs through initial coordination forming h2-H2 intermediates, followed subsequent hydride transfer Q DHQ ligands (migratory insertion reductive elimination, respectively). Except elimination THQ product, all elementary steps were reversible, which is an important point in connection with hydrogen storage models. Our theoretical DFT calculations are consistent experimental results previously reported.

Язык: Английский

Процитировано

0