Homobimetallic Ruthenium(II) Complexes Catalysed Selective Transfer Hydrogenation of Aldehydes in Water DOI
Gopal Deshmukh, Thakur Rochak Kumar Rana, Gopalan Rajaraman

et al.

Chemistry - An Asian Journal, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 12, 2024

Abstract Herein we report chemoselective transfer hydrogenation (TH) of aldehydes in aqueous medium using a series homobimetallic Ru(II) catalysts. Two complexes ( Ru1 and Ru3 ) one monometallic complex Ru2 have been employed the catalytic reduction aldehydes. Bimetallic [( p ‐cymene) 2 (RuCl) L 3 ] is obtained from reaction Schiff base ligand 2,2′‐((1E,1′E)‐((3,3′,5,5′‐tetraisopropyl‐[1,1′‐biphenyl]‐4,4′diyl)bis(azaneylylidene))bis(methaneylylidene))bis(4‐bromophenol) H characterized by various spectroscopic analytical techniques. The use formic acid/formate buffer as hydride source catalyst loading 0.01 mol % or resulted conversion to corresponding alcohols good excellent yield. This method very efficient for selective presence other reducible functional groups. A 0.0001 sufficient achieve turnover frequency (TOF) 5.5×10 5 h −1 . Furthermore, can recycled reused six consecutives cycles without sacrificing efficiency. comparison results between bimetallic offers valuable insights into distinct reactivity patterns complexes, presumably originating cooperative effect. To understand detailed mechanism, explored mechanistic pathway DFT methods on reported catalysts models which indicate that addition aldehyde rate‐limiting cooperativity boost efficiency case dinuclear catalyst. pH dependent TH mechanism has investigated with aid NMR ESI‐MS

Language: Английский

Expanding Diversity of Fused Steroid-Quinoline Hybrids by Sequential Amination/Annulation/Aromatization Reactions DOI Creative Commons

Caterina Momoli,

Antonio Arcadi, Marco Chiarini

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 7, 2025

Viable alternative approaches to a variety of ring A and D-fused steroid-quinoline hybrids, along with A, D-fused, and/or A-fused, side chain-substituted steroid-bis-quinolines were explored by means sequential amination/annulation/aromatization reactions suitable ketosteroids 2-acyl-substituted anilines. Key factors directing the chemoselective behavior polyfunctionalized substrates investigated. Remarkably, use TMSOTf as an promoter/catalyst enabled direct synthesis desired avoiding protection/deprotection steps conventional procedures when starting contained labile functional groups.

Language: Английский

Citations

0
Ru-CNP Complex-Catalyzed Hydrogen Transfer/Annulation Reaction of 2-Nitrobenzylalcohol via an Outer-Sphere Mechanism DOI
Z. Zhao, Yinyin Chen, Chunchun Zhang

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 3, 2025

The development of efficient catalysts plays a central role in advancing chemical reactions. In this study, ruthenium complex modified with N-heterocyclic carbene-imine-phosphine ligand (CNP) was employed to enhance the hydrogen transfer/annulation process 2-nitrobenzyl alcohols various primary or secondary alcohols. NMR and HRMS analyses reaction solution revealed situ formation [fac-RuH(CO)(PPh3)(κ3-CN(H)P)]Cl through transfer hydrogenation imine moiety within CNP under conditions. This species, bifunctional Noyori-type featuring facial coordination CN(H)P ligand, served as key catalytic intermediate. By leveraging outer-sphere mechanism facilitated by [fac-RuH(CO)(PPh3)(κ3-CN(H)P)]Cl, synthesis 75 quinolines from wide range has been achieved yields high 95%.

Language: Английский

Citations

0
Homobimetallic Ruthenium(II) Complexes Catalysed Selective Transfer Hydrogenation of Aldehydes in Water DOI
Gopal Deshmukh, Thakur Rochak Kumar Rana, Gopalan Rajaraman

et al.

Chemistry - An Asian Journal, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 12, 2024

Abstract Herein we report chemoselective transfer hydrogenation (TH) of aldehydes in aqueous medium using a series homobimetallic Ru(II) catalysts. Two complexes ( Ru1 and Ru3 ) one monometallic complex Ru2 have been employed the catalytic reduction aldehydes. Bimetallic [( p ‐cymene) 2 (RuCl) L 3 ] is obtained from reaction Schiff base ligand 2,2′‐((1E,1′E)‐((3,3′,5,5′‐tetraisopropyl‐[1,1′‐biphenyl]‐4,4′diyl)bis(azaneylylidene))bis(methaneylylidene))bis(4‐bromophenol) H characterized by various spectroscopic analytical techniques. The use formic acid/formate buffer as hydride source catalyst loading 0.01 mol % or resulted conversion to corresponding alcohols good excellent yield. This method very efficient for selective presence other reducible functional groups. A 0.0001 sufficient achieve turnover frequency (TOF) 5.5×10 5 h −1 . Furthermore, can recycled reused six consecutives cycles without sacrificing efficiency. comparison results between bimetallic offers valuable insights into distinct reactivity patterns complexes, presumably originating cooperative effect. To understand detailed mechanism, explored mechanistic pathway DFT methods on reported catalysts models which indicate that addition aldehyde rate‐limiting cooperativity boost efficiency case dinuclear catalyst. pH dependent TH mechanism has investigated with aid NMR ESI‐MS

Language: Английский

Citations

0