Rh-Catalyzed Hydrogenative One-Pot Protocol for the Synthesis of Saturated N-Heterocycles DOI
Mark Lautens, Jeanne Masson‐Makdissi

Synfacts, Journal Year: 2022, Volume and Issue: 18(08), P. 0866 - 0866

Published: July 18, 2022

Language: Английский

Asymmetric arene hydrogenation: towards sustainability and application DOI Creative Commons

Lukas Lückemeier,

Marco Pierau,

Frank Glorius

et al.

Chemical Society Reviews, Journal Year: 2023, Volume and Issue: 52(15), P. 4996 - 5012

Published: Jan. 1, 2023

This review summarises the state-of-the-art in transition-metal catalysed asymmetric hydrogenation of (hetero)arenes and highlights recent advances with a special focus on sustainability while also addressing its shortcomings.

Language: Английский

Citations

53
Machine learning prediction of nitrogen heterocycles in bio-oil produced from hydrothermal liquefaction of biomass DOI
Lijian Leng, Weijin Zhang, Qingyue Chen

et al.

Bioresource Technology, Journal Year: 2022, Volume and Issue: 362, P. 127791 - 127791

Published: Aug. 17, 2022

Language: Английский

Citations

45
cis-Selective Hydrogenation of Aryl Germanes: A Direct Approach to Access Saturated Carbo- and Heterocyclic Germanes DOI Creative Commons
Akash Kaithal, Himadri Sekhar Sasmal, Subhabrata Dutta

et al.

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(7), P. 4109 - 4118

Published: Feb. 13, 2023

A catalytic approach of synthesizing the cis-selective saturated carbo- and heterocyclic germanium compounds (3D framework) is reported via hydrogenation readily accessible aromatic germanes (2D framework). Among numerous catalysts tested, Nishimura's catalyst (Rh2O3/PtO2·H2O) exhibited best reactivity with an isolated yield up to 96%. broad range substrates including synthesis unprecedented was explored. This selective strategy could tolerate several functional groups such as −CF3, −OR, −F, −Bpin, −SiR3 groups. The synthesized products demonstrated applications in coupling reactions newly developed aza-Giese-type addition reaction (C–N bond formation) from cyclic germane product. These versatile motifs can have a substantial value organic medicinal chemistry they show orthogonal while competing other partners boranes or silanes, acquiring three-dimensional structure high stability robustness.

Language: Английский

Citations

18
Ru-NHC-Catalyzed Asymmetric, Complete Hydrogenation of Indoles and Benzofurans: One Catalyst with Dual Function DOI Creative Commons
Fuhao Zhang, Himadri Sekhar Sasmal, Constantin G. Daniliuc

et al.

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(29), P. 15695 - 15701

Published: July 12, 2023

The highly enantioselective and complete hydrogenation of protected indoles benzofurans has been developed, affording facile access to a range chiral three-dimensional octahydroindoles octahydrobenzofurans, which are prevalent in many bioactive molecules organocatalysts. Remarkably, we control the nature ruthenium N-heterocyclic carbene complex employed as both homogeneous heterogeneous catalysts, providing new avenues for its potential applications asymmetric more challenging aromatic compounds.

Language: Английский

Citations

17
Improving reproducibility through condition-based sensitivity assessments: application, advancement and prospect DOI Creative Commons
Felix Schäfer,

Lukas Lückemeier,

Frank Glorius

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(36), P. 14548 - 14555

Published: Jan. 1, 2024

The fluctuating reproducibility of scientific reports presents a well-recognised issue, frequently stemming from insufficient standardisation, transparency and lack information in publications.

Language: Английский

Citations

5
Nickel‐Catalyzed Sequential Dehydrogenation and Cyclization of 2‐Amino(Nitro)‐benzyl Alcohols with Alkyl Alcohols: Synthesis of C‐3‐Substituted Quinolines DOI

Motahar Sk,

Atanu Bera, Debasis Banerjee

et al.

ChemCatChem, Journal Year: 2023, Volume and Issue: 15(11)

Published: April 26, 2023

Abstract We herein reported a general and efficient Ni‐catalyzed protocol for sequential double de‐hydrogenative cyclization of 2‐amino(nitro)‐benzyl alcohols with primary to C‐3‐substituted quinolines releasing water dihydrogen as by products. As special highlight, late stage functionalization cholesterol derivative including chemo‐selective transformations citronellol, fatty acid derived oleyl alcohol long chain C 4 −C 14 alkyl were reported. Initial mechanistic studies deuterium‐labelling experiments perform establish the cyclization.

Language: Английский

Citations

11
Divergent Hydrogenation of Indoles and Its Applications in Total Syntheses of (±)-α- and γ-Lycoranes DOI

Shoule Han,

Mingliang Lou,

Xiaolei Liu

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 45(3), P. 913 - 913

Published: Jan. 1, 2025

Language: Английский

Citations

0
Applying green chemistry principles to iron catalysis: mild and selective domino synthesis of pyrroles from nitroarenes DOI Creative Commons
Johannes Fessler, Kathrin Junge, Matthias Beller

et al.

Chemical Science, Journal Year: 2023, Volume and Issue: 14(41), P. 11374 - 11380

Published: Jan. 1, 2023

An efficient and general cascade synthesis of pyrroles from nitroarenes using an acid-tolerant homogeneous iron catalyst is presented. Initial (transfer) hydrogenation the commercially available iron-Tetraphos followed by acid catalysed Paal-Knorr condensation. Both formic molecular hydrogen can be used as green reductants in this process. Particularly, under transfer conditions, shows remarkable reactivity at low temperatures, high functional group tolerance excellent chemoselectivity transforming a wide variety substrates. Compared to classical heterogeneous catalysts, system presents complementing reactivity, showing none typical side reactions such dehalogenation, debenzylation, arene or olefin hydrogenation. It thereby enhances chemical toolbox terms orthogonal reactivity. The methodology was successfully applied late-stage modification multi-functional drug(-like) molecules well one-pot bioactive agent BM-635.

Language: Английский

Citations

10
Achieving High Affinity for a Bacterial Lectin with Reversible Covalent Ligands DOI
Giulia Antonini, Anna Bernardi,

Émilie Gillon

et al.

Journal of Medicinal Chemistry, Journal Year: 2024, Volume and Issue: 67(21), P. 19546 - 19560

Published: Oct. 31, 2024

High-affinity monovalent ligands for lectins are challenging to develop due weak binding interactions. This study investigates the potential of rationally designed covalent targeting N-terminal domain BC2L-C lectin from Burkholderia cenocepacia, a pathogen causing severe respiratory infections in immunocompromised patients. Antiadhesion therapy is emerging as complementary approach against such infections, and bacterial suitable targets. The fucose-specific BC2L-C-Nt recognizes blood group oligosaccharides on host cells. Using computational approach, we reversible competitive that include fucoside anchor salicylaldehyde warhead Lys108 near fucose-binding site. Several candidates were synthesized tested using competition experiments. most effective ligand improved IC50 methyl-fucoside by 2 orders magnitude, matching affinity native H-type 1 trisaccharide. Control experiments confirmed importance both fucose moiety ligand's affinity. Mass analysis interaction with Lys108.

Language: Английский

Citations

3
Synthesis of Saturated N‐Heterocycles via a Catalytic Hydrogenation Cascade DOI Creative Commons

Tobias Wagener,

Marco Pierau,

Arne Heusler

et al.

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(19), P. 3366 - 3371

Published: June 9, 2022

Saturated N-heterocycles are prominent motifs found in various natural products and pharmaceuticals. Despite the increasing interest this class of compounds, synthesis saturated bicyclic azacycles requires tedious multi-step syntheses. Herein, we present a one-pot protocol for octahydroindoles, decahydroquinolines, octahydroindolizines through cascade reaction.

Language: Английский

Citations

15