Regioselective C(sp³) Carboboration of 1,3-Diynes: A Direct Route to Fully Substituted Enyne Boronates

Organic Letters, Journal Year: 2024, Volume and Issue: 26(31), P. 6574 - 6579

Published: July 29, 2024

Here, we report a general copper-catalyzed C(sp3) carboboration of 1,3-diynes, providing access to an array tetra-substituted boryl enynes in regioselective manner. All four positions enyne can be efficiently manipulated using this methodology. The reaction was smoothly applied the conjugation complex bioactive molecules scaffold. Cross-coupling reactions were carried out with boron end groups on densely substituted 1,3-enynes, opening avenues for modular synthesis highly functionalized enynes. Control experiments and density functional theory studies supported proposed mechanism.

Language: Английский

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Heteroaryl Group Containing Trisubstituted Alkenes: Synthesis and Anti‐tumor Activity

Chemistry & Biodiversity, Journal Year: 2024, Volume and Issue: 21(11)

Published: Aug. 15, 2024

Abstract Pancreatobililary cancers are fatal solid tumors that pose a significant threat to human life. It is imperative investigate novel small molecule active compounds for controlling these cancers. Heterocyclic (e. g. gemcitabine) and multi‐substituted alkenes resveratrol) commonly applied in tumor treatment. Researchers have proposed the synthesis of new trisubstituted containing heteroaromatic rings by combining two scaffolds may be fresh strategy develop molecules. In this study, we utilized alkenyl bromide heteroaryl boronic acid as substrates, employing Suzuki coupling generate series triarylethylenes featuring nitrogen, oxygen, sulfur atoms. Through vitro experiments, results indicated some exhibited remarkable anti‐tumor efficacy IC50 [ 3be , GBC‐SD] =0.13 μM PANC‐1] =0.27 μM). The further demonstrated antitumor was dependent on heteroatom, π‐system, skeleton‐bonding site, substituent type.

Language: Английский

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Diether‐Based Chiral Multilayered 3D Polymers and Oligomers: Unveiling AIE and AIP Phenomena

Macromolecular Chemistry and Physics, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 14, 2024

Abstract In this study, the synthesis of a novel chiral multilayer 3D polymer based on diether structure is reported. This architecture not only imparts chirality but also facilitates study aggregation‐induced emission (AIE) and polarization (AIP). Using various polymerization techniques, multilayered structures are constructed that exhibit significant AIE, marked by increased luminescence upon aggregation, notable AIP behavior, indicating enhanced optical activity. Comprehensive characterization through spectroscopy microscopy elucidates mechanisms behind these phenomena. These findings highlight potential diether‐based polymers for advanced optoelectronic sensor applications, paving way multifunctional materials.

Language: Английский

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Synthesis and Characterization of Multilayer 3D Chiral Polymers with Enhanced Optical Properties

Molecules, Journal Year: 2025, Volume and Issue: 30(7), P. 1567 - 1567

Published: March 31, 2025

This study reports the synthesis of novel multilayer 3D chiral polymers using 2,2′-(2,7-Naphthalenediyl)bis[4,4,5,5-tetramethyl-1,3,2-dioxaborolane] and 1,8-dibronaphthalene along with its derivatives as key precursors. Comprehensive characterization was performed nuclear magnetic resonance (NMR), gel permeation chromatography (GPC), photoluminescence, ultraviolet (UV) spectroscopy, scanning electron microscopy (SEM), polarimetry, dynamic light scattering (DLS), thermogravimetric analysis (TGA). Notably, exhibited remarkable aggregation-induced emission (AIE) polarization (AIP) phenomena, revealing enhanced luminescence optical activity in aggregated states. These findings underscore potential these for applications optoelectronics advanced sensing technologies, highlighting intricate relationship between molecular structure behavior.

Language: Английский

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Synthesis of 1,5-Diamino-Substituted 1,3-Dienes via Rhodium(II)-Catalyzed Tandem Reactions of 1-Cyclopropylethylarenes

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 18, 2025

Herein, (E,E)-1,5-diamino-1,3-dienes are stereoselectively synthesized from substituted aryl derivatives via a rhodium(II)-catalyzed C(sp3)-H functionalization involving cascade of cyclopropane ring expansion, cyclobutene formation, to 1,3-diene conversion, and regioselective diamination. Mechanistic studies show this one-pot process proceeds through hydrogen atom transfer (HAT), radical-polar crossover (RPC), elimination, electrocyclic ring-opening, radical addition, underscoring rhodium(II)'s role in radical-mediated catalysis beyond traditional rhodium(II) nitrenoid chemistry.

Language: Английский

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Advanced green synthesis: Solvent-free and catalyst-free reaction

Green Synthesis and Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 1, 2024

Language: Английский

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Copper(I)‐Catalyzed Proto/Carboboration of Enyne Boronates for the Synthesis of Densely Substituted Diene Diboronates

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 12, 2024

Abstract A copper‐catalyzed carbo‐/protoboration of boryl enynes is disclosed, providing access to an array penta‐ and hexasubstituted diboryl dienes in a chemo‐, regio‐ stereoselective manner. All six positions the can be manipulated using this methodology. The diene boronates adopt skew conformation. An iterative Suzuki coupling products provided highly conjugated trienes tetraenes.

Language: Английский

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