Thioarylation of Alkynes to Generate Dihydrothiopheniums through Gold(I)/(III)-Catalyzed Cyclization–Cross-Coupling DOI
Joseph A. Kaplan,

Jonghyun Won,

Suzanne A. Blum

et al.

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

Published: Sept. 14, 2024

A thioarylation method is developed for the synthesis of 2,3-dihydrothiopheniums through an electrophilic-cyclization-cross-coupling mechanism, harnessing gold(I)/(III) cycle recently MeDalPhosAuCl catalyst. Single-crystal X-ray crystal structural analysis dihydrothiophenium products characterized antiaddition sulfur and Csp

Language: Английский

Electronic Effects of Bidentate P,N-Ligands on the Elementary Steps of Au(I)/Au(III) Reactions Relevant to Cross-Coupling Chemistry DOI Creative Commons
Joseph W. Treacy, Elaine Y. Chao, Grace E. Kunkel

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 9, 2024

Oxidant-free Au(I)/Au(III)-catalyzed cross-coupling has been recently enabled by the use of bidentate

Language: Английский

Citations

5
Gold-Catalyzed Deallylative C–S Cross-Coupling Reactions DOI

Prafulla Bera,

Tanmayee Nanda,

Nivrutti B. Barhate

et al.

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

Published: May 1, 2025

Herein, we report the gold-catalyzed deallylative C-S cross-coupling reaction through ligand-enabled Au(I)/Au(III) redox catalysis. One of major challenges in reactions is to prevent catalyst deactivation caused by formation a strong gold-sulfur bond. We discovered that use allyl phenyl sulfide as sulfur surrogate facilitates dynamic equilibrium between cationic Au(I) and Au(I)-sulfide complexes, overcoming gold quenching problem. A detailed mechanistic investigation, including 31P NMR studies, mass analysis, stoichiometric experiments, provided valuable insights into mechanism, which further supported computational studies.

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
Thioarylation of Alkynes to Generate Dihydrothiopheniums through Gold(I)/(III)-Catalyzed Cyclization–Cross-Coupling DOI
Joseph A. Kaplan,

Jonghyun Won,

Suzanne A. Blum

et al.

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

Published: Sept. 14, 2024

A thioarylation method is developed for the synthesis of 2,3-dihydrothiopheniums through an electrophilic-cyclization-cross-coupling mechanism, harnessing gold(I)/(III) cycle recently MeDalPhosAuCl catalyst. Single-crystal X-ray crystal structural analysis dihydrothiophenium products characterized antiaddition sulfur and Csp

Language: Английский

Citations

0