Non-classical effective methods for reduction of heteroaromatic compounds DOI
Yu. Yu. Titova, А. В. Иванов

Russian Chemical Reviews, Journal Year: 2024, Volume and Issue: 93(11), P. RCR5149 - RCR5149

Published: Oct. 30, 2024

The review summarizes the known data on various methods for saturation and dearomatization of heterocyclic moieties, forming diverse aromatic compounds. Since classical hydrogenation substrates with molecular hydrogen has a number fundamental drawbacks that hinder both its use at laboratory level widespread implementation in industrial production, main attention is paid to non-classical described literature over last 20–25years. ammonia-free Birch reduction, transfer hydrogenation, reduction by Hantzsch esters some other reactions involving compounds are summarized systematized. It shown such or heterocycles can cases be more efficient than procedures.<br> bibliography includes 173 references.

Language: Английский

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

et al.

Catalysis Science & Technology, Journal Year: 2024, Volume and Issue: 14(17), P. 4843 - 4847

Published: Jan. 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.

Language: Английский

Citations

5
Iron(II) triflate as a photocatalyst for trifluoromethylation of functionalized arenes under blue LED light: Access to bioactive compounds DOI
Sandeep Kumawat, Kishore Natte

Journal of Catalysis, Journal Year: 2024, Volume and Issue: 434, P. 115506 - 115506

Published: April 20, 2024

Language: Английский

Citations

4
Dearomative selective reduction of structurally diverse N-heteroarenes enabled by a homogeneous titanium catalyst DOI
Tarun Kumar Bhatt,

Vitisha Suman,

Mridula Choudhary

et al.

Journal of Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 115937 - 115937

Published: Jan. 1, 2025

Language: Английский

Citations

0
2.3 Chemoselective Hydrogenation of Heteroarenes DOI
Zackaria Nairoukh, Hanming Ding, Michael Z. Hu

et al.

Published: Jan. 1, 2025

Abstract The hydrogenation of heteroarenes is considered one the most valuable synthetic tools, converting unsaturated, flat into their corresponding aliphatic analogues. However, when reactive functional groups are present, achieving chemoselectivity becomes a major challenge. This review highlights importance overcoming this challenge by demonstrating value obtained products, which can be incorporated synthesis complex architectures.

Language: Английский

Citations

0
Stable Meisenheimer Complexes as Powerful Photoreductants Readily Obtained from Aza‐Heteroaromatic Compounds DOI Creative Commons
Francesco Calogero,

Leonie Wilczek,

Emanuele Pinosa

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(44)

Published: July 30, 2024

Abstract Excited states of radical anions derived from the photoreduction stable organic molecules are suggested to serve as potent reductants. However, excited these species too short‐lived allow bimolecular quenching processes. Recently, singlet state Meisenheimer complexes, which possess a long‐lived state, was identified competent for reduction challenging substrates (−2.63 V vs. SCE, saturated calomel electrode). To produce reasonably and simply accessible different addition n BuLi readily available aromatic heterocycles investigated, photoreactivity generated studied. In this paper, we present straightforward preparation family powerful photoreductants (*E ox < −3 SCE in their states, determined by DFT time‐dependent TD‐DFT calculations; DFT, density functional theory) that can induce dehalogenation electron‐rich aryl chlorides form C−C bond through cyclization. Photophysical analyses computational studies combination with experimental mechanistic investigations demonstrate ability adduct act strong electron donor under visible light irradiation.

Language: Английский

Citations

2
Methyl Formate, an Alternative Transfer Hydrogenating Agent for Chemoselective Reduction of N-Heteroarenes and Azoarenes DOI

Anirban Sau,

Divya Mahapatra,

Ankur Maji

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(21), P. 4486 - 4491

Published: May 21, 2024

The search for efficient molecular hydrogen precursors and their catalytic exploration is necessary the evolution of transfer hydrogenation. Methyl formate (MF) having high content still remains unexplored such transformations. Herein, we disclosed a bifunctional Ir(III)-complex catalyzed chemoselective TH protocol N-heteroarenes azoarenes using MF. A variety substrates including ten bioactive molecules have been synthesized under mild reaction conditions. probable mechanistic pathway was proposed based on control experiments studies.

Language: Английский

Citations

1
Ammonia-Borane Dependent Transfer Hydrogenation of Carboxylic Esters to Primary Alcohols DOI
Sandeep Kumawat,

Suravi Dey,

Kishore Natte

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(15), P. 10719 - 10728

Published: July 11, 2024

Here, we present a user-friendly protocol that uses bench-stable NH

Language: Английский

Citations

1
Stable Meisenheimer Complexes as Powerful Photoreductants Readily Obtained from Aza‐Heteroaromatic Compounds DOI Creative Commons
Francesco Calogero,

Leonie Wilczek,

Emanuele Pinosa

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(44)

Published: July 30, 2024

Abstract Excited states of radical anions derived from the photoreduction stable organic molecules are suggested to serve as potent reductants. However, excited these species too short‐lived allow bimolecular quenching processes. Recently, singlet state Meisenheimer complexes, which possess a long‐lived state, was identified competent for reduction challenging substrates (−2.63 V vs. SCE, saturated calomel electrode). To produce reasonably and simply accessible different addition n BuLi readily available aromatic heterocycles investigated, photoreactivity generated studied. In this paper, we present straightforward preparation family powerful photoreductants (*E ox < −3 SCE in their states, determined by DFT time‐dependent TD‐DFT calculations; DFT, density functional theory) that can induce dehalogenation electron‐rich aryl chlorides form C−C bond through cyclization. Photophysical analyses computational studies combination with experimental mechanistic investigations demonstrate ability adduct act strong electron donor under visible light irradiation.

Language: Английский

Citations

0
Non-classical effective methods for reduction of heteroaromatic compounds DOI
Yu. Yu. Titova, А. В. Иванов

Russian Chemical Reviews, Journal Year: 2024, Volume and Issue: 93(11), P. RCR5149 - RCR5149

Published: Oct. 30, 2024

The review summarizes the known data on various methods for saturation and dearomatization of heterocyclic moieties, forming diverse aromatic compounds. Since classical hydrogenation substrates with molecular hydrogen has a number fundamental drawbacks that hinder both its use at laboratory level widespread implementation in industrial production, main attention is paid to non-classical described literature over last 20–25years. ammonia-free Birch reduction, transfer hydrogenation, reduction by Hantzsch esters some other reactions involving compounds are summarized systematized. It shown such or heterocycles can cases be more efficient than procedures.<br> bibliography includes 173 references.

Language: Английский

Citations

0