Synthesis of Aryl Alkyl Thioethers via a Copper-Catalyzed Three-Component Reaction with DABSO, Aryldiazonium Salts, and Alkyl Bromides DOI

Nithin Pootheri,

Sunwoo Lee

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 11, 2024

We developed a method for synthesizing aryl alkyl thioether compounds via three-component reaction involving aryldiazonium salts, 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide), and bromides. Optimal yields were achieved when copper catalyst was used in conjunction with zinc tetrabutylammonium bromide an acetonitrile solvent at 130 °C 10 h. This methodology demonstrates good functional group tolerance enables the successful synthesis of various thioethers moderate to high yields.

Language: Английский

Direct C(sp3)-H functionalization with aryl and alkyl radicals as intermolecular hydrogen atom transfer (HAT) agents DOI
Jia‐Lin Tu, Binbin Huang

Chemical Communications, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Recent years have witnessed the emergence of direct intermolecular C(sp

Language: Английский

Citations

6
Synthesis of Dithioester Derivatives by Base-Mediated Fragmentation of 1,3-Dithiolanes DOI Creative Commons

Hasan Pelit,

Mehmet Aytug Sinmaz,

Oyku Acelya Ildem

et al.

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

Published: April 14, 2025

Dithioesters are important agents for chain transfer in polymer chemistry and precursors the synthesis of heterocycles. Straightforward approaches to their therefore demand. Outlined herein is a method access such compounds one-pot. 2-Aryl-1,3-dithiolanes undergo ring fragmentation with LiHMDS CPME generate aryl-dithiocarboxylates 5 min at 100 °C. These anions subsequently captured second step by addition various alkyl halides diaryliodonium salts furnish large library dithioesters good yields. The can be also employed one-pot, one-step manner bromides allows gram scale.

Language: Английский

Citations

0
Direct Synthesis of Ethers from Alcohols & Aldehydes Enabled by an Oxocarbenium Ion Interception Strategy DOI Creative Commons
D. P. CURRAN,

Marcin Szydło,

Helge Müller-Bunz

et al.

Chemical Science, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

While a combination of alcohol and aldehyde under acidic conditions typically gives an acetal, interception the intermediate oxocarbenium ion by phosphine followed hydrolysis leads to ethers without need for hydride donor.

Language: Английский

Citations

0
Programmable Strategies for the Conversion of Aldehydes to Unsymmetrical (Deuterated) Diarylmethanes and Diarylketones DOI Creative Commons
Vipin R. Gavit, Nicole Hanania, Nadim Eghbarieh

et al.

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

Published: March 28, 2025

Herein, we present a versatile method for synthesizing unsymmetrical diarylmethanes and diarylketones from aldehydes arenes. This involves: (1) regioselective Ar-H alkylation to form benzhydrylphosphonium salts via one-pot, four-component reaction with simple reagents (2) chemoselective reductions or oxidations of the benzylic C-P bond. Notably, D2O yield fully deuterated diarylmethanes. high-yielding, straightforward approach offers valuable building blocks enables novel transformations academic pharmaceutical research.

Language: Английский

Citations

0
Electroreductive Carboxylation of Benzylphosphonium salts with CO2 Through the Cleavage of the C(sp3)-P Bond DOI

Fen Han,

Fenfen Xie,

Mengyun Yin

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(28), P. 5724 - 5728

Published: Jan. 1, 2024

Herein, a novel electroreductive carboxylation of benzylphosphine salts with CO 2 through cleavage the C(sp 3 )-P bond was reported under conditions without redox reagents and noble metal catalysts.

Language: Английский

Citations

2
1-Hydroxyalkylphosphonium Salts—Synthesis and Properties DOI Creative Commons
Jakub Adámek, Anna Kuźnik, Agnieszka Październiok-Holewa

et al.

Molecules, Journal Year: 2023, Volume and Issue: 29(1), P. 18 - 18

Published: Dec. 19, 2023

An efficient and convenient method for the synthesis of 1-hydroxyalkylphosphonium salts is described. Reactions were carried out at room temperature, in a short time, without chromatography product isolation. The properties obtained phosphonium examined discussed. In this paper, primary attention was paid to stability salts, depending on structure aldehydes used as substrates their preparation. Other conditions such type solvent, molar ratio also investigated. Finally, high reactivity demonstrated reactions with amide-type (hetero)aromatic compounds. developed step-by-step procedure (with isolation 1-hydroxyphosphonium salts) compared one-pot protocol (in situ formation salts).

Language: Английский

Citations

2
Synthesis of Aryl Alkyl Thioethers via a Copper-Catalyzed Three-Component Reaction with DABSO, Aryldiazonium Salts, and Alkyl Bromides DOI

Nithin Pootheri,

Sunwoo Lee

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 11, 2024

We developed a method for synthesizing aryl alkyl thioether compounds via three-component reaction involving aryldiazonium salts, 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide), and bromides. Optimal yields were achieved when copper catalyst was used in conjunction with zinc tetrabutylammonium bromide an acetonitrile solvent at 130 °C 10 h. This methodology demonstrates good functional group tolerance enables the successful synthesis of various thioethers moderate to high yields.

Language: Английский

Citations

0