Synthesis of Chiral Biphenyl Monophosphines as Ligands in Enantioselective Suzuki–Miyaura Coupling DOI

Hong-Yu Qu,

Wen‐Hua Zheng

Organic Letters, Год журнала: 2023, Номер 25(51), С. 9119 - 9123

Опубликована: Дек. 19, 2023

Herein, we describe our design and synthesis of novel chiral monophosphine ligands by the short-step addition lactates as side chains to well-known ligand SPhos/RuPhos. The new were shown be highly efficient in palladium-catalyzed Suzuki-Miyaura coupling, providing a series axially biphenyl products high yield enantioselectivity. Furthermore, gram-scale reaction diverse conversions demonstrated potential utility approach.

Язык: Английский

Metal‐Catalyzed Enantioselective Cleavage of Aromatic C−O Bonds DOI
Yu‐Sheng Su, Zhi‐Chao Cao

ChemCatChem, Год журнала: 2024, Номер 16(12)

Опубликована: Апрель 18, 2024

Abstract Phenol derivatives are naturally abundant or can be easily fabricated from commercially accessible building blocks. In recent years, with the aim of producing functionally important chiral compounds in enantioenriched form, there has been initial progress development metal‐catalyzed cross‐coupling reactions that involve enantioselective cleavage aromatic C−O bonds. This concept encompasses a review significant advancements this field, as well associated strategies. Moreover, challenges and potential opportunities area also underscored.

Язык: Английский

Процитировано

2

The therapeutic efficacy of different configuration nano-polydopamine drug carrier systems with photothermal synergy against head and neck squamous cell carcinoma DOI Creative Commons
Yuhao Guo, Bo Li, Huixu Xie

и другие.

Regenerative Biomaterials, Год журнала: 2024, Номер 11

Опубликована: Янв. 1, 2024

Abstract Head and neck squamous cell carcinoma (HNSCC) is the sixth most common malignant tumor worldwide. Considering its special anatomical site progressive resistance to chemotherapy drugs, development of more effective, minimally invasive precise treatment methods urgently needed. Nanomaterials, given their properties, can be used as drug carrier systems improve therapeutic effect reduce adverse effects. The with photothermal promote killing cancer cells help overcome through heat stress. We selected dopamine, a simple raw material, designed synthesized three different configurations nano-polydopamine (nPDA) nanomaterials, including nPDA balls, plates porous balls. In addition self-polymerization self-assembly, has high conversion efficiency easily modified. Moreover, we loaded cisplatin into nPDA, creating nPDA-cis (the nano-drug system cisplatin), comparatively studied properties antitumor effects all materials in vitro vivo. found that balls had synergistic cisplatin, resulting excellent good clinical application prospects. comparison suggested importance optimizing spatial configuration design examining physical chemical future systems. this study, also noted duality complexity influences stress on tumors specific mechanisms synergy immunotherapy will an important research direction future.

Язык: Английский

Процитировано

2

Atroposelective Synthesis of Biaryl N‐Oxides via Cu‐Catalyzed De Novo Heteroaromatic N‐Oxide Ring Formation DOI Creative Commons
Ke Ma, Ting Qi, Lei Hu

и другие.

Advanced Science, Год журнала: 2024, Номер 11(40)

Опубликована: Авг. 9, 2024

Abstract Heteroaromatic N ‐oxides, renowned for their highly polar N─O bond and robust structure, exhibit significant bioactivities have played a pivotal role in various drug development projects since the discovery of Minoxidil. Moreover, heteroaromatic featuring axially chiral biaryl frameworks, are indispensable as Lewis base catalysts ligands organic synthesis. Despite importance, synthesizing these compounds is challenging, necessitating starting materials or resolution processes. Catalytic strategies rely on functionalization ‐oxide compounds, leading to products with relatively limited skeletal diversity. This study introduces Cu‐catalyzed atroposelective method ‐oxides via de novo ring formation. mild efficient approach achieves excellent stereoselectivities (up 99:1 er), enabling production wide array novel scaffolds. The product 3f demonstrates high stereoselectivity recyclability catalyst. Additionally, 3e exhibits promising therapeutic efficacy against triple‐negative breast cancer, IC 50 values 4.8 5.2 µ m MDA‐MB‐231 MDA‐MB‐468 cells, respectively. research not only advances synthesis challenging but also encourages further exploration entities bioactive small molecules.

Язык: Английский

Процитировано

2

Atropselective Organocatalytic Synthesis of Chiral Compounds Containing Nitrogen along the Axis of Chirality DOI Open Access
Ana Maria Faísca Phillips, Armando J. L. Pombeiro

Symmetry, Год журнала: 2023, Номер 15(6), С. 1261 - 1261

Опубликована: Июнь 15, 2023

Atropisomers, i.e., stereoisomers that are distinct because their free rotation about a single bond is hindered by steric interactions between nearby bulky groups or electrostatics, may interact with surroundings in different ways, and also exhibit properties. They be found as natural products, pharmaceutical agricultural active ingredients, chiral ligands organocatalysts, functional materials. Our ability to synthesize them stereoselectively sustainable way, using achiral materials simply the aid of an organocatalyst mild conditions, has become hot topic research. This review provides overview recent achievements synthesis atropisomers containing C-N N-N axes chirality.

Язык: Английский

Процитировано

5

Synthesis of Chiral Biphenyl Monophosphines as Ligands in Enantioselective Suzuki–Miyaura Coupling DOI

Hong-Yu Qu,

Wen‐Hua Zheng

Organic Letters, Год журнала: 2023, Номер 25(51), С. 9119 - 9123

Опубликована: Дек. 19, 2023

Herein, we describe our design and synthesis of novel chiral monophosphine ligands by the short-step addition lactates as side chains to well-known ligand SPhos/RuPhos. The new were shown be highly efficient in palladium-catalyzed Suzuki-Miyaura coupling, providing a series axially biphenyl products high yield enantioselectivity. Furthermore, gram-scale reaction diverse conversions demonstrated potential utility approach.

Язык: Английский

Процитировано

4