Pyrrolylsulfonium salts: stable, accessible and versatile pseudohalides for Stille couplings DOI Creative Commons
Jodie L. Hann, Catherine L. Lyall, Gabriele Kociok‐Köhn

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Pyrroles functionalised with a thianthrenium or diphenylsulfonium group undergo Stille couplings aryl alkynyl stannanes in good yields, avoiding the issues of instability that can hamper use analogous pyrrolyl halides.

Language: Английский

Palladium-Catalyzed Domino Conversion of Aryl–Thianthreniums with Anhydrides: Rapidly Building Highly Functionalized Fluorenones DOI
Jiang Nan, Haiyan Xiao, Yangmin Ma

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(16), P. 3332 - 3337

Published: April 15, 2024

As a class of rising electrophilic coupling reagents, aryl–thianthreniums (aryl-TTs) have been gaining immense attention. Herein, novel palladium-catalyzed domino annulation aryl-TTs with anhydrides is proposed to rapidly assemble collection highly functionalized fluorenones. This finding presents an innovative reaction pattern wherein the version first involved. Heavily compared existing conversions aryl-TTs, this identified process successively functions as four aryl C–H bonds.

Language: Английский

Citations

9
Electroreductive Arylcarboxylation of Styrenes with CO2 and Aryl Halides via a Radical–Polar Crossover Mechanism DOI

Fenfen Xie,

Fen Han,

Qian Su

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(21), P. 4427 - 4432

Published: May 17, 2024

2,3-Diaryl propanoic acids are important structures as a result of their widespread presence in numerous bioactive compounds. However, the limitations existing synthetic techniques include requirement for costly catalysts and limited substrates. Here, we developed novel electroreductive arylcarboxylation alkenes with CO2 based on radical–polar crossover pathway assisted by easily accessible dimethyl terephthalate reductive mediator. This method will provide an efficient strategy synthesis 2,3-diarylpropanoic acids.

Language: Английский

Citations

8
Visible light-promoted defluorinative alkylation/arylation of α-trifluoromethyl alkenes with thianthrenium salts DOI
Yue Zhang, Jianyou Mao, Zhihong Wang

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(17), P. 9371 - 9377

Published: Jan. 1, 2024

Defluorinative alkylation and arylation between thianthrenium salts α-trifluoromethyl alkene to afford gem -difluoroolefins by easily recycling thianthrene under visible light irradiation free of metal photocatalyst.

Language: Английский

Citations

8
Palladium-Catalyzed Hiyama-Type Coupling of Thianthrenium and Phenoxathiinium Salts DOI

Zhiwei Cao,

J. Zhang,

Jintao Wang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(31), P. 6681 - 6686

Published: July 26, 2024

Here, we demonstrate palladium-catalyzed Hiyama-type cross-coupling reactions of aryl thianthrenium or phenoxathiinium salts. By employing stable and inexpensive organosilanes, the arylation, alkenylation, alkynylation were realized in high efficiency using commercially available Pd(tBu3P)2 as catalyst, thus providing a reliable method for preparation biaryls, styrenes, acetylenes with broad functional group tolerance under mild conditions. Given accessibility salts from simple arenes remarkable regioselective fashion, this protocol also provides an attractive approach late-stage modification complex bioactive scaffolds.

Language: Английский

Citations

4
Visible Light-Induced Radical Cascade Functionalization of Quinoxalin-2(1H)-ones: Three-Component 1,2-Di(hetero)arylation Approach with Styrenes and Thianthrenium Salts DOI

Sudip Sau,

Shinobu Takizawa, Hun Young Kim

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(41), P. 8821 - 8826

Published: Oct. 9, 2024

The additive-free visible light-induced three-component 1,2-di(hetero)arylation of styrenes was developed using quinoxalin-2(1

Language: Английский

Citations

4
Mechanochemically Induced Thianthrenium Salts-Based Arylation of Diverse Heterocyclic Scaffolds DOI
Raman Kumar, Anoop Sharma, Anuj Sharma

et al.

ACS Sustainable Chemistry & Engineering, Journal Year: 2024, Volume and Issue: 12(34), P. 12808 - 12818

Published: Aug. 15, 2024

Herein, a mechanochemically triggered C–H arylation of coumarins, quinoline-N-oxides, and uracil molecules with aryl thianthrenium salts is described. Aryl are primarily acknowledged for their expedient reusability adherence to atom economy principles. Mechanistic studies suggested that mechanical stress promoted the homolytic scission C–S bond salts, forming radical intermediate. Later, intermediate engaged in addition reaction above heterocycles, leading desired products good yields. This versatile protocol accommodates wide range functional groups facilitates synthesis bioactive compounds drug molecules.

Language: Английский

Citations

3
Alkene Carboxy-Alkylation via CO2•– DOI
Yun Dang, Jimin Han, Alyah F. Chmiel

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(51), P. 35035 - 35042

Published: Dec. 12, 2024

Herein, we introduce a new platform for alkene carboxy-alkylation. This reaction is designed around CO

Language: Английский

Citations

3
Unusual Regio‐ and Chemoselectivity in Oxidation of Pyrroles and Indoles Enabled by a Thianthrenium Salt Intermediate DOI Creative Commons
Jodie L. Hann, Catherine L. Lyall, Gabriele Kociok‐Köhn

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: unknown

Published: June 3, 2024

A dearomative oxidation of pyrroles to Δ

Language: Английский

Citations

2
Stabilized Carbon Radical‐Mediated Assembly of Arylthianthrenium Salts, Alkenes and Amino Acid/Peptide Derivatives DOI Creative Commons

Bo Dong,

Weiguan Qi,

Yifeng Chen

et al.

Advanced Science, Journal Year: 2024, Volume and Issue: 12(2)

Published: Nov. 21, 2024

Abstract Efficiently assembling amino acids and peptides with bioactive molecules facilitates the modular streamlined synthesis of a diverse library peptide‐related compounds. Particularly notable is their application in pharmaceutical development, leveraging site‐selective late‐stage functionalization. Here, visible light‐induced three‐component reaction involving arylthianthrenium salts, acid/peptide derivatives, alkenes are introduced. This approach utilizes captodatively‐stabilized carbon radicals to enable radical‐radical C─C coupling, effectively constructing complex molecules. method offers promising alternative route for peptide‐derived bio‐relevant compounds

Language: Английский

Citations

1
Photoredox-catalyzed synthesis of α,α-difluoromethyl-β-alkoxysulfones from sulfur dioxide DOI

Minjun Yin,

Lin Yuhui,

Manli Zhuang

et al.

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: unknown, P. 109926 - 109926

Published: April 1, 2024

Language: Английский

Citations

0