General Synthesis of Conformationally Constrained Noncanonical Amino Acids with C(sp3)-Rich Benzene Bioisosteres DOI
Xiaoshen Ma, Adam Beard, Samantha A. Burgess

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(7), P. 5010 - 5018

Published: March 27, 2024

Recent years have seen novel modalities emerge for the treatment of human diseases resulting in an increase beyond rule 5 (bRo5) chemical matter. As a result, synthetic innovations aiming to enable rapid access complex bRo5 molecular entities become increasingly valuable medicinal chemists' toolkits. Herein, we report general synthesis new class noncanonical amino acids (ncAA) with cyclopropyl backbone achieve conformational constraint and bearing C(sp3)-rich benzene bioisosteres. We also demonstrate preliminary studies toward utilities these ncAA as building blocks chemistry research.

Language: Английский

Metal-organic framework-based nanostructured catalysts: Applications in efficient organic transformations DOI
Changlei Xia, Jiamin Wu, Seyed Ali Delbari

et al.

Molecular Catalysis, Journal Year: 2023, Volume and Issue: 546, P. 113217 - 113217

Published: May 27, 2023

Language: Английский

Citations

30

Enantiocovergent Cross-Coupling Reaction with 1,4-Dihydropyridine Derivatives via Photoinduced Nickel Catalysis DOI
Tongtong Li, Lifeng Luo, Xiaokai Cheng

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(5), P. 3278 - 3286

Published: Feb. 15, 2024

Herein, we reported the enantioconvergent Csp3–Csp2 cross-coupling reaction with 1,4-dihydropyridine (DHP) derivatives via photoredox/nickel dual catalysis to access chiral products good yield and enantioselectivity. The operationally simple was carried out under mild conditions functional group tolerance. Due use of a stoichiometric equivalent aryl/alkenyl halides as coupling partners, sequential iterative synthesis could be achieved smoothly in one pot for position isomers stereoisomers. In proposed mechanism, kinetic experiments mechanistic studies indicated that radical generation, depended on excited photocatalyst DHP, rate-determining step.

Language: Английский

Citations

9

Palladium installed copper-organic framework for C–C coupling reactions DOI
Yumei Wang,

Mei-Xia Tao,

Kai‐Ming Mo

et al.

Science China Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 3, 2025

Language: Английский

Citations

1

Photothermally Enhanced Dual Enzyme‐mimic Activity of Gold‐Palladium Hybrid Nanozyme for Cancer Therapy DOI
Yan Kang, Chao Li,

Huali Shi

et al.

Chinese Journal of Chemistry, Journal Year: 2023, Volume and Issue: 41(23), P. 3189 - 3196

Published: July 11, 2023

Comprehensive Summary Based on characteristics of the tumor microenvironment (TME), including acidity, hypoxia, inflammation and hydrogen peroxide overload, combined with emerging nanotechnologies, designing nanoplatforms TME specificity/responsiveness for treatment is a promising nanotherapeutic strategy. In this work, multifunctional gold‐palladium bimetallic cascade nanozyme was constructed effective photothermal‐enhanced catalyzed synergistic therapy tumors. The dumbbell‐like Au‐Pd nanomaterial (Au NRs‐Pd@HA) obtained by reducing palladium gold nanorods ascorbic acid (AA) further modified hyaluronic (HA). introduction HA brings biocompatibility targeting properties. zebrafish embryos model showed that Au NRs‐Pd@HA had good low biotoxicity. can induce catalytic conversion glucose to generate H 2 O efficiently, subsequently undergo reaction produce abundant ·OH radicals, exhibiting peroxidase‐like (POD‐like) oxidase‐like (GOD‐like) capabilities. generated key factor ablation. Meanwhile, exhibits photothermal performance under 808 nm irradiation, in favor (PTT). Especially, POD‐like GOD‐like activities were significantly enhanced due effect. PTT nanozymes effect enabled efficient safe cancer therapy.

Language: Английский

Citations

17

Synthesis of Alkynylsilanes: A Review of the State of the Art DOI
Krzysztof Kuciński

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(11), P. 2382 - 2431

Published: April 12, 2024

Abstract This contribution offers a comprehensive overview of methods for forging sp C−Si bonds. Over time, alkynylsilanes (silylacetylenes), once considered mere byproducts hydrosilylation processes, have become essential building blocks in organic synthesis. literature review traces the evolution their synthesis, from traditional methodologies relying on organolithium and organomagnesium compounds to more advanced cross‐coupling reactions involving hydro‐ carbosilanes. Focused primarily past 25 years (2000–2024), it also extensively references significant historical breakthroughs. By analyzing synthetic methodologies, not only survey current state knowledge but identifies areas improvement. Furthermore, emphasize importance 1‐alkynylsilanes (1‐silyl‐1‐alkynes), selected applications these are highlighted, confirming potential

Language: Английский

Citations

6

A Half Century of the Sonogashira Reaction DOI

Stephanie Frankenberger,

Dominik Wendinger,

Alexander Scherer

et al.

Organic reactions, Journal Year: 2025, Volume and Issue: unknown, P. 1 - 1149

Published: Jan. 3, 2025

Conjugated alkynes are valuable intermediates in the synthesis of natural products, agrochemicals, pharmaceuticals, fine chemicals, and organic molecular materials. Since its introduction 1975, palladium‐catalyzed Sonogashira reaction has become primary choice for construction sp–sp 2 carbon–carbon bonds aryl‐, heteroaryl‐, alkenyl‐substituted alkynes. A vast range conditions have been explored to expand optimize scope reaction, including sustainable variants, microwave‐assisted cross couplings, couplings performed water. Research efforts also target development improved catalytic systems such as solid‐supported palladium catalysts nanoparticles, use N ‐heterocyclic carbenes (NHCs) ligands, well copper‐free variants reaction. This Chapter reviews application coupling terminal with aryl or alkenyl halides triflates. Coupling reactions that form conjugated via alternative methods, different electrophiles, catalysts, alkynes, briefly described.

Language: Английский

Citations

0

Photochemical Sonogashira coupling reactions: beyond traditional palladium–copper catalysis DOI
P. R. SINGH, Aslam C. Shaikh

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(78), P. 11615 - 11630

Published: Jan. 1, 2023

This review briefly summarizes the developments in photochemical Sonogashira-coupling reactions. It especially highlights underlying mechanisms for formation of C–C bond and photocatalyst evolution towards sustainability.

Language: Английский

Citations

10

Sulfoxides as electrophilic substrates in cross-coupling reactions DOI
Rahadian Zainul, Bahaa Fadhil Hamzah, Hussein Ali Al‐Bahrani

et al.

Journal of Sulfur Chemistry, Journal Year: 2025, Volume and Issue: unknown, P. 1 - 14

Published: Feb. 25, 2025

Language: Английский

Citations

0

Palladium-Catalyzed Sonogashira Cross-Couplings of (Hetero)Aryl Fluorosulfates DOI

Kathleen M. Morrison,

Giulio Volpin, Sherif J. Kaldas

et al.

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

Published: March 4, 2025

The palladium-catalyzed Sonogashira cross-coupling of (hetero)aryl fluorosulfates and terminal alkynes, featuring a synthetically useful scope yields, is reported herein. Such transformations involving diversity fluorosulfate coupling partners, including chemoselective examples where contending chloro functionalities are present, achieved using DPPF/[Pd(cinnamyl)Cl]2 catalyst system without the requirement copper additive.

Language: Английский

Citations

0

A heterogeneous MOF-253-based Pd/Cu bimetal for Sonogashira coupling reactions DOI

Ningtao Cao,

Yue Tong, Jianwei Xie

et al.

Tetrahedron, Journal Year: 2025, Volume and Issue: unknown, P. 134628 - 134628

Published: March 1, 2025

Language: Английский

Citations

0