Gold-Catalyzed Alkenylation and Arylation of Phosphorothioates DOI Creative Commons

Urvashi Urvashi,

Sampoorna Mishra,

Nitin T. Patil

et al.

Published: Sept. 4, 2023

Reported herein is the gold-catalyzed alkenylation and arylation of phosphorothioates using alkenyl aryl iodides. The facile transmetalation between Ag-sulfur complex Au(III) intermediate formed after oxidative addition key to success this transformation. This methodology operates under mild reaction conditions with catalyst loading as low 1 mol%, thereby providing an efficient access biologically active S-alkenyl S-aryl

Language: Английский

Gold-Catalyzed C–N Cross-Coupling Reactions of Aryl Iodides with Alkyl Nitriles or Silver Cyanate DOI
Hongyan Liu, Bo Xu

Organic Letters, Journal Year: 2024, Volume and Issue: 26(26), P. 5430 - 5435

Published: June 24, 2024

We have gold-catalyzed C–N cross-couplings of aryl iodides with aliphatic nitriles. Although nitriles are usually challenging nitrogen cross-coupling partners, they could be activated by base-mediated deprotonation and isomerization. The method utilizes widely available substrates in moderate to good yields provide various N-aryl compounds. In addition, a similar strategy extended the silver cyanate. protocol features high humidity/air tolerance works inter- intramolecularly.

Language: Английский

Citations

3
Mannitol‐based CO Surrogate for Palladium‐Catalyzed Alkoxycarbonylation DOI Creative Commons

Z. W. Liu,

Hefei Yang,

Zhipeng Bao

et al.

European Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 6, 2025

Abstract Carbonylative transformation is already been accepted as a powerful toolbox in synthetic chemistry. However, the manipulation of toxic and smell‐less carbon monoxide gas lagged it from wide range applications. Hence developing new efficient CO surrogates become an attractive topic. Herein, we developed novel mannitol‐based surrogate with enhanced loading capacity compared to known organic surrogates. We successfully used palladium‐catalyzed alkoxycarbonylation aryl bromides phenols only 0.5 equivalent required. This newly designed offers additional possibility for further development

Language: Английский

Citations

0
Gold‐Catalyzed Alkyne‐Amine Cascade Annulations: A Modern Strategy for Azaheterocycle Construction DOI
Alexey Yu. Dubovtsev

The Chemical Record, Journal Year: 2025, Volume and Issue: unknown

Published: April 7, 2025

Abstract Gold catalysis has experienced remarkable progress over the past two decades, particularly in transformations involving alkynes. While numerous aspects of gold‐catalyzed reactions have been extensively reviewed, specific area cascade annulations between functionalized amines and alkynes represents a distinct rapidly developing direction that warrants focused attention. This survey collects systematically analyzes these transformations, which emerged as convenient synthetic strategies to diverse nitrogen heterocycles. The relevant are classified firstly by chemical nature amine functional substituent, secondly size formed ring. field under consideration bridges several fundamental practical branches chemistry, including catalysis, organic synthesis, medicinal materials science.

Language: Английский

Citations

0
Preparation of gold nanoparticles decorated UiO-66-NH2 incorporated epichlorohydrin and cyclodextrin as novel efficient catalyst in cross coupling and carbonylative reactions DOI Creative Commons
Leila Mohammadi,

Mohammad Reza Vaezi

Scientific Reports, Journal Year: 2025, Volume and Issue: 15(1)

Published: April 25, 2025

Language: Английский

Citations

0
Halogenation of aromatic compounds with N-halosuccinimides (NXS) catalyzed by D-camphorsulfonic acid‒BiCl3 DOI
Kiyoshi Tanemura

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(25), P. 5105 - 5111

Published: Jan. 1, 2024

Aromatic bromination catalysed by 0.5-10 mol% of D-camphorsulfonic acid-BiCl3 with

Language: Английский

Citations

3
Synthesis of Aryl Thiocyanates, Aryl Dithiocarbamates, Aryl Sulfones, and Aryl Thiobenzoates via Au-Catalyzed C–S Cross-Couplings DOI
Hongyan Liu, Guifang Chen, Bo Xu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(46), P. 9835 - 9840

Published: Nov. 11, 2024

We have developed an efficient gold-catalyzed C-S cross-coupling of various silver-based thionucleophiles with aryl iodides. Our method offers a one-stop-shop solution for synthesizing diverse sulfur-containing aromatics, including thiocyanic acids, diethyldithiocarbamates, sulfones, and thiobenzoates. protocol gives moderate to excellent yields compatibility functional groups. In comparison other transition-metal-catalyzed cross-couplings, our has advantages in broad applicability high tolerance toward air moisture.

Language: Английский

Citations

3
Silver-Catalyzed Coupling of Unreactive Carboxylates: Synthesis of α-Fluorinated O-Aryl Esters DOI
Kotaro Kikushima,

Keina Komiyama,

Narumi Umekawa

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(25), P. 5347 - 5352

Published: June 17, 2024

α-Fluorinated aryl esters pose a challenge in synthesis via O-arylation of α-fluorinated carboxylates owing to their low reactivities. This limitation has been addressed by combining silver catalyst with aryl(trimethoxyphenyl)iodonium tosylates access esters. We envision that the catalytic system involves high-valent species generated oxidation silver(I) salt. The present method provided synthetic protocol for various including fluorinated analogs drug derivatives.

Language: Английский

Citations

2
Gold‐Catalyzed Arylative Cope Rearrangement DOI
Bidisha Paroi, Chayanika Pegu, Manoj V. Mane

et al.

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

Published: May 21, 2024

Abstract Cope rearrangements have garnered significant attention owing to their ability undergo structural reorganization in stereoselective manner. While substantial advances been achieved over decades, these remained applicable exclusively parent 1,5‐hexadienes. Herein, we disclose the gold‐catalyzed arylative rearrangement of 1,6‐heptadienes via a cyclization‐induced [3,3]‐rearrangement employing ligand‐enabled gold redox catalysis. Detailed mechanistic investigations including several control experiments, cross‐over experiment, HRMS analysis, 31 P NMR and DFT studies performed underpin mechanism.

Language: Английский

Citations

0
Ligand‐Enabled Gold‐Catalyzed Cyanation of Organohalides DOI Open Access
Anil Kumar, Nandita Bhattacharya, Manoj V. Mane

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(47)

Published: Aug. 12, 2024

Abstract Herein, we disclose the first report on gold‐catalyzed C(sp 2 )‐CN cross‐coupling reaction by employing a ligand‐enabled Au(I)/Au(III) redox catalysis. This transformation utilizes acetone cyanohydrin as nucleophilic cyanide source to convert simple aryl and alkenyl iodides into corresponding nitriles. Combined experimental computational studies highlighted crucial role of cationic silver salts in activating stable (P,N)‐AuCN complex towards oxidative addition subsequently generate key aryl‐Au(III) complexes.

Language: Английский

Citations

0
Gold-Catalyzed Alkenylation and Arylation of Phosphorothioates DOI Creative Commons

Urvashi Urvashi,

Sampoorna Mishra,

Nitin T. Patil

et al.

Published: Sept. 4, 2023

Reported herein is the gold-catalyzed alkenylation and arylation of phosphorothioates using alkenyl aryl iodides. The facile transmetalation between Ag-sulfur complex Au(III) intermediate formed after oxidative addition key to success this transformation. This methodology operates under mild reaction conditions with catalyst loading as low 1 mol%, thereby providing an efficient access biologically active S-alkenyl S-aryl

Language: Английский

Citations

1