A Computational mechanistic study on the Ni-Catalyzed Asymmetric Alkynyl Propyl Hydroxyaminations: Origin of Enantioselectivity and Further Rational Design DOI
Yuqing Huang,

Manman Zhu,

Shuqi Zhang

et al.

New Journal of Chemistry, Journal Year: 2024, Volume and Issue: 48(28), P. 12565 - 12574

Published: Jan. 1, 2024

DFT calculations were conduct to elucidate the catalytic mechanism of target asymmetric propargylic substitution (APS) reaction. Moreover, we rationally designed a more efficient axial chiral phosphine ligand for APS

Language: Английский

Anchoring Ag(I) into MOF-253 for Effectively Catalyzing Cycloaddition of CO2 with Alkynyl Alcohols/Amine under Ambient Conditions DOI
Chao‐Ying Gao,

Lin Ding,

Yang Li

et al.

Inorganic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 26, 2025

In the era of global warming, conversion carbon dioxide into high-value products has become a widely scrutinized emerging mitigation strategy. Metalation bpy-containing MOF-253 led to synthesis MOF-253-0.5Ag, which acts as an efficient catalyst for carbonylative cyclization CO2 with alkyne molecules (such propynyl alcohols and amines) at room temperature ambient pressure, yielding corresponding α-alkyl cyclic carbonates oxazolidinones, thus endowing catalytic system bifunctional characteristics. Additionally, MOF-253-0.5Ag demonstrated stability, high activity, recyclability. The mechanisms were further elucidated through experimental results NMR analysis, demonstrating that Ag(I) can effectively activate C≡C bonds hydroxy/amino groups substrates.

Language: Английский

Citations

0
The literature of heterocyclic chemistry, part XXII, 2022 DOI
Галина А. Газиева, Yu. B. Evdokimenkova, N. O. Soboleva

et al.

Advances in heterocyclic chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Language: Английский

Citations

0
Propargyl Amines: Versatile Building Blocks in Post‐Ugi Transformations DOI Creative Commons

Rinkal B. Bhoraniya,

Sachin G. Modha

ChemistryOpen, Journal Year: 2023, Volume and Issue: 12(4)

Published: Jan. 31, 2023

Abstract The Ugi reaction, a multicomponent allows diversity‐oriented synthesis Its importance is recognized by an exponential increase in the publications utilizing post‐Ugi transformations as strategy to build complex molecules via simple and sustainable processes recent literature. A second concept, alkyne activation through metal‐, acid‐, iodine‐catalysis base‐mediated transformations, also leads wonderful short efficient synthetic routes. Combination of these two approaches application alkyne‐containing component reaction brings benefits both protocols into one sequence. propargyl amines come obvious choice this context they work wonderfully amine while has potential generate biologically interesting carbo‐ hetero‐cyclic systems. Thus, can compare adduct with pupa which inherent property metamorphosis molecules. In review, discussed focus on transformations.

Language: Английский

Citations

9
Amine-catalyzed metal-free deamination of propargylamines with water toward chalcones DOI
Pengyu Zhou, Liliang Huang,

Yujuan Xie

et al.

Molecular Catalysis, Journal Year: 2022, Volume and Issue: 534, P. 112808 - 112808

Published: Nov. 18, 2022

Language: Английский

Citations

9
Synthesis of Polysubstituted Furan Frameworks via [3 + 2] Annulation of N-Enoxyimides with Chelated Alkynes Initiated by Rh(III)-Catalyzed C–H Activation DOI
Min Wu, Yi Wang, Jing Zhou

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(14), P. 2394 - 2399

Published: April 3, 2023

A variety of 2,3,5-trisubstituted furans were synthesized by virtue a Rh(III)-catalyzed vinylic C-H coupling N-enoxyimides with propargyl alcohols or amines. In this protocol, served as one-oxygen and two-carbon synthon the -OH/-NHR moiety in alkynes was found to be crucial for realizing desired chemo-/regioselectivity. Detailed experimental mechanistic studies together DFT calculations clarified sequential activation/regioselective alkyne insertion/simultaneous O-N bond cleavage hydrogen transfer/intramolecular nucleophilic addition/aromatization reaction path, which involved distinctive Rh(V) carbene species active intermediate.

Language: Английский

Citations

4
Recent Advances in the Synthesis of N-Heterocycles via Lewis acid-Catalyzed/Mediated Cyclization of Propargyl- and Homopropargyl-amines and their Derivatives DOI
Bipin Kumar Behera,

Priya Ghosh,

Anil K. Saikia

et al.

Tetrahedron, Journal Year: 2024, Volume and Issue: 162, P. 134123 - 134123

Published: Aug. 1, 2024

Language: Английский

Citations

1
Regioselective Reversal in One-Pot and Two-Step Reaction of 1-(2-Hydroxyphenyl)-Propargyl Alcohols with Aryl/Alkyl Mercaptan: Construction of 3-(Alkylthio)benzofurans and 2-(Alkylthiomethyl)benzofurans Starting from Identical Materials DOI

Yang Zhu,

Guisheng Deng

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 7, 2024

The Cu(MeCN)4PF6-catalyzed reaction of 1-(2-hydroxyphenyl)-propargyl alcohols with aryl/alkyl mercaptan and subsequent treatment K2CO3 only offered 3-(alkylthio)benzofurans, whereas the stoichiometric-exceeding CuI-mediated DIPEA furnished 2-(alkylthiomethyl)benzofurans high selectivity. amount Cu(I) salts plays a key role in selective formation. This unique protocol for construction two series benzofurans containing alkylthio group proved to be suitable broad substrates 1 2 except aliphatic alkynyl alcohols.

Language: Английский

Citations

1
Alkyne Activation in the Diversity Oriented Synthesis of sp2‐Rich Scaffolds: A Biased Library Approach for Targeting Polynucleotides (DNA/RNA) DOI Creative Commons
Shuqi Chen, Daniel L. Priebbenow, Julie Somkhit

et al.

Chemistry - A European Journal, Journal Year: 2022, Volume and Issue: 28(71)

Published: Sept. 7, 2022

Polynucleotides, DNA and RNA (mRNA non-coding RNAs) are critically involved in the molecular pathways of disease. Small molecule binding interactions with polynucleotides can modify functional polynucleotide topologies and/or their proteins. Current approaches to library design (lead-like or fragment-like libraries) based on protein-ligand often include careful consideration 3-dimensional orientation motifs exclude π-rich compounds (polyfused aromatics) avoid off-target R/DNA interactions. In contrast proteins, where π,π-interactions weak, form strong suitable ligands. To assist designing a polynucleotide-biased library, scaffold-divergent synthesis approach polyfused aromatic scaffolds has been undertaken. Initial screening hits that moderately stable polynucleotide-ligand-protein ternary complexes be further optimized through judicious incorporation substituents scaffold increase An example this is given for topoisomerase-1 (TOP1), generating novel TOP1 inhibitory chemotype.

Language: Английский

Citations

5
Base-catalyzed addition of silylacetylenes to ketones: a route to protected tertiary propargyl alcohols DOI Creative Commons
Krzysztof Kuciński,

Alicja Łuczak,

Aliaksei Mankouski

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(11), P. 2752 - 2759

Published: Jan. 1, 2023

Novel protocol for base-catalyzed addition of silylacetylenes to ketones – exceptional scope, gram scale and derivatization.

Language: Английский

Citations

2
Regioselective Propargylic Suzuki–Miyaura Coupling by SciPROP-Iron Catalyst DOI
S. -M. Lu, Ryosuke Agata,

Satsuki Nomura

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(12), P. 8385 - 8396

Published: April 29, 2024

The iron-catalyzed Suzuki–Miyaura cross-coupling of secondary propargyl electrophiles with lithium organoborates has been established. A propyl-bridged bulky bisphosphine ligand, SciPROP-TB, cooperated the TIPS substituent at alkyne terminal position to achieve reaction exclusive propargylic selectivity. features high functional group compatibility, regioselectivity, and yield a broad substrate scope. an optically active chiral bromide proceeds complete racemization, supporting mechanism involving radical formation.

Language: Английский

Citations

0