Perfluoroalkyl‐Decorated Noble‐Metal‐Free MOFs for the Highly Efficient One‐Pot Four‐Component Coupling between Aldehydes, Amines, Alkynes, and Flue Gas CO2 DOI
Fan Yang, Jiajia Wang, You Wang

et al.

Angewandte Chemie, Journal Year: 2023, Volume and Issue: 136(6)

Published: Dec. 20, 2023

Abstract The non‐noble‐metal catalysed‐multicomponent reactions between flue gas CO 2 and cheap industrial raw stocks into high value‐added fine chemicals is a promising manner for the ideal utilization route. To achieve this, key fundamental challenge rational development of highly efficient facile reaction pathway while establishing compatible catalytic system. Herein, through stepwise solvent‐assisted linker installation, post‐synthetic fluorination metalation, we report construction series perfluoroalkyl‐decorated noble‐metal‐free metal–organic frameworks (MOFs) PCN‐(BPY‐CuI)‐(TPDC‐F x ) [BPY=2,2′‐bipyridine‐5,5′‐dicarboxylate, TPDC‐NH =2′‐amino‐[1,1′:4′,1′′‐terphenyl]‐4,4′′‐dicarboxylic acid] that can catalyze one‐pot four‐component alkyne, aldehyde, amine preparation 2‐oxazolidinones. Such assembly endows MOFs with superhydrophobic microenvironment, superior water resistance stable site, leading to 21 times higher turnover numbers than homogeneous counterparts. Mechanism investigation implied substrates be efficiently enriched by MOF wall then adsorbed species act as an extrinsic binding site towards dilute their strong preferential formation carbamate acid. Moreover, density functional theory calculations suggest tetrahedral geometry Cu in offers special poisoning, thus maintaining its efficiency during process.

Language: Английский

Recent advances in fixation of CO2 into organic carbamates through multicomponent reaction strategies DOI
Lu Wang, Chaorong Qi, Wenfang Xiong

et al.

CHINESE JOURNAL OF CATALYSIS (CHINESE VERSION), Journal Year: 2022, Volume and Issue: 43(7), P. 1598 - 1617

Published: May 21, 2022

Language: Английский

Citations

68
E/Z Photoisomerization of Olefins as an Emergent Strategy for the Control of Stereodivergence in Catalysis DOI Creative Commons
Javier Corpas, Pablo Mauleón, Ramón Goméz Arrayás

et al.

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(8), P. 1348 - 1370

Published: March 5, 2022

Abstract The stereoselective photoisomerization of olefins via Energy Transfer (E n T) sensitization bears significant potential in the context rational design catalytic stereodivergent methodologies. Whereas approaches for controlling access to E‐ and Z ‐ isomers depend highly on nature catalyst – therefore are not easily implemented as a general strategy E T catalysis has emerged recent years an increasingly powerful tool olefin geometry control nearly perfect step‐economic fashion. Moreover, this approach presents both high functional group tolerance and, most notably, demonstrated ample multicatalytic compatibility. This feature enabled development tandem strategies, which focus Review. magnified image

Language: Английский

Citations

45
Updates on hypervalent-iodine reagents: metal-free functionalisation of alkenes, alkynes and heterocycles DOI
Anjali Dahiya, Ashish Kumar Sahoo, Nikita Chakraborty

et al.

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(10), P. 2005 - 2027

Published: Jan. 1, 2022

Hypervalent iodine (HVI) chemistry is a rapidly growing subdomain of contemporary organic because its enormous synthetic applications. The high nucleofugality the phenyliodonio group (-I+Ph) and radical nature, serving as single-electron oxidant makes HVI compounds highly valuable in synthesis. Due to feasibility benignity, reactions that rely solely on reagents promoters have received particular interest. Considering their great influence potential, we contribute brief synopsis this field with specific emphasis metal-free functionalisations alkenes, alkynes heterocycles. discussion divided according type substrate reaction elaborated mechanism representative examples.

Language: Английский

Citations

34
Thermally Activated Delayed Fluorescence Sensitizers As Organic and Green Alternatives in Energy-Transfer Photocatalysis DOI
Ryoga Hojo,

Alexander M. Polgar,

Zachary M. Hudson

et al.

ACS Sustainable Chemistry & Engineering, Journal Year: 2022, Volume and Issue: 10(30), P. 9665 - 9678

Published: July 21, 2022

Photocatalysis has captured the imagination of synthetic chemists and is poised to become a staple fine chemical industry. Over past decade, subfield energy-transfer (EnT) catalysis expanded dramatically, harnessing excited states photosensitizer unlock variety redox-neutral, radical-based reactivities in mild selective fashion. However, many developments this discipline rely on precious rare earth metals such as iridium. This perspective will highlight rise thermally activated delayed fluorescence (TADF) materials metal-free alternatives EnT photocatalysis for organic transformations. Emphasis be placed recent progress cycloadditions, E/Z isomerization olefins, other radical-initiated processes; all mediated by mechanism Dexter energy transfer. The tunable excited-state energetics dynamics TADF allow them effectively compete with iridium-based sensitizers, indicating their promise green organocatalysis.

Language: Английский

Citations

27
Photoredox-catalyzed coupling of aryl sulfonium salts with CO2and amines to accessO-aryl carbamates DOI
Yanhui Guo, Wei Li,

Zhonglin Wen

et al.

Chemical Communications, Journal Year: 2022, Volume and Issue: 59(6), P. 764 - 767

Published: Dec. 13, 2022

An efficient photoredox-catalyzed three-component coupling reaction of aryl sulfonium salts, carbon dioxide and amines has been developed for the first time. This provides a new strategy synthesis range valuable O-aryl carbamates from readily available arenes via site-selective thianthrenation/carbamoyloxylation two-step process. Mild conditions, broad substrate scope good functional group tolerance are features transformation. The synthetic utility method was demonstrated by late-stage modification bioactive molecules pharmaceuticals.

Language: Английский

Citations

19
Catalyst-Enabled Stereodivergence in Photochemical Atom Transfer Radical Addition (ATRA) of α-Iodoboronic Esters to Alkynes DOI

Qi Fan,

Jiawu Huang,

Shuang Lin

et al.

ACS Catalysis, Journal Year: 2023, Volume and Issue: 14(1), P. 299 - 307

Published: Dec. 16, 2023

The atom transfer radical addition (ATRA) to alkynes is a valuable strategy for the synthesis of allylic substituted molecules, yet it has not been applied boronic acids or their esters, which are important building blocks in organic synthesis. inherent challenge ATRA reactions control geometric selectivity. By employing different alkene isomerization techniques, namely, photochemical uphill catalysis and manganese-catalyzed halogen-abstraction/radical rebound processes, we able synthesize both isomers iodinated esters stereoselective manner. Mechanistic investigations reveal dual functionalities catalysts, acting as catalysts processes. protocols feature broad substrate scope good functional group tolerance. Importantly, iodo boryl moieties within products provide orthogonal handles further synthetic manipulations. employed here should inspire more efforts toward alkynes.

Language: Английский

Citations

11
Cyclic Diphenylchloronium-Salt-Triggered Coupling of Sulfides with Nucleophiles: Modular Assembly of Pharmaceuticals DOI

Bangxiong Kang,

Wei Li, Huanfeng Jiang

et al.

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

Published: April 2, 2025

We report a novel coupling strategy enabled by cyclic diphenylchloronium salt that facilitates reactions between sulfides and diverse nucleophiles, including oxygen- nitrogen-based species. The methodology efficiently produces structurally varied valuable compounds, carbamates, carboxylic esters, aryl ethers, alkylated amines, under mild, operationally simple conditions. protocol's synthetic utility was highlighted through modular preparation of five important drugs structural analogues, demonstrating significant potential for drug discovery applications.

Language: Английский

Citations

0
Palladium-Catalyzed Reductive Formylation of Aryl Iodides with CO2 under Mild Conditions DOI
Dan Li, Wei Li, Wenfang Xiong

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(8), P. 5231 - 5237

Published: Jan. 16, 2023

A palladium-catalyzed reductive formylation of aryl iodides with carbon dioxide as the carbonyl source under mild reaction conditions was realized by using a combination Pd(PCy3)2Cl2 and di-2-pyridyl ketone catalyst phenylsilane reagent, leading to variety aromatic aldehydes in moderate excellent yields. The protocol features wide substrate scope, good functional group tolerance, simple operation.

Language: Английский

Citations

10
Palladium‐Catalyzed Carbonylation of Aryl Sulfonium Salts with CO2 as a CO Surrogate DOI
Y. P. Guo, Wei Li, Huanfeng Jiang

et al.

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 13(7)

Published: April 9, 2024

Abstract Palladium‐catalyzed carbonylation of aryl sulfonium salts with CO 2 as a surrogate has been successfully developed via one‐pot two‐step procedure. Thus, by merging thianthrenation and the carbonylation, site‐selective aromatic C−H plethora readily available arenes can be realized , providing access to variety structurally diverse useful benzamides, esters carboxylic acids. Simple operation, broad substrate scope, good functional group tolerance mild reaction conditions are attractive features method. Late‐stage functionalization complex bioactive molecules well precise synthesis pharmaceuticals 1‐BCP butoxycaine demonstrated potential application established protocol.

Language: Английский

Citations

3
Silver-Catalyzed Coupling of Ethynylbenziodoxolones with CO2 and Amines to Afford O-β-Oxoalkyl Carbamates DOI
Wei Li, Yanhui Guo, Ziyang Li

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(22), P. 4600 - 4605

Published: May 23, 2024

A novel three-component coupling reaction of ethynylbenziodoxolones (EBXs) with CO

Language: Английский

Citations

3