Chelating-Group-Assisted C(sp2)–O Reductive Elimination at the Gold(III) Center DOI
Avishek Das, Sadhana Tripathi, Lisa Roy

et al.

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

Published: May 1, 2025

Herein, we demonstrate chelating-group-assisted C(sp2)-O reductive elimination at gold(III) centers. Detailed stoichiometric studies highlighted the importance of a chelating group for achieving successful C-O elimination, paving way development catalytic version. The mechanistic investigations, including control experiments, 31P NMR, mass spectrometry, and density functional theory (DFT) studies, suggested that synergistic effect ligand creates highly coordinated environment around Au(III) center to facilitate bond-forming reaction.

Language: Английский

In Silico Screening of P,N-Ligands Facilitates Optimization of Au(III)-Mediated S-Arylation DOI Creative Commons
Joseph W. Treacy, James A. R. Tilden, Elaine Y. Chao

et al.

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

Published: Jan. 1, 2025

In silico examination of 13 P , N -ligated Au( iii ) OACs determined the key mechanistic factors governing )-mediated S -arylation. Three complexes were synthesized which exhibited bimolecular coordination rate constants as high 20 200 M −1 s .

Language: Английский

Citations

2
Gold-Catalyzed 1,2-Carboxyarylation of Alkenes DOI
Tanmayee Nanda, Avishek Das,

Prafulla Bera

et al.

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

Published: Feb. 24, 2025

Herein, we disclose an unprecedented gold-catalyzed 1,2-carboxyarylation of alkenes through ligand-enabled Au(I)/Au(III) catalysis. Unlike other approaches for the arylative functionalization C-C multiple bonds, attempts to utilize weak nucleophiles such as carboxylate anions were unsuccessful. The key achieving this transformation is use a 1,3-diketone-appended alkene, which undergoes oxyarylation followed by retro-aldol reaction afford product. Detailed mechanistic investigations conducted support proposed mechanism.

Language: Английский

Citations

0
Exploring the Electronic and Steric Effects of Hemilabile (P^N) Ligands in Redox Gold Catalysis: Application to the Cross-Coupling Reaction of Aliphatic Amines with Aryl Iodides DOI

Urvashi Urvashi,

Saurabh Rai, Gaurav Shukla

et al.

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

Published: Feb. 28, 2025

Herein, we report 17 new (P^N) ligands for redox gold catalysis, featuring various substituents at -C4, -C5, and -C6 of the aryl ring nitrogen handle. Rate kinetics experiments revealed that electron-rich -C4 -C5 positions enhanced rate oxidative addition Au(I) with C(sp2)-Br bonds compared to electron-poor substituents. Further, an unprecedented gold-catalyzed arylation aliphatic amines using electronically rich ligand (L6) -OMe group position.

Language: Английский

Citations

0
Gold-Catalyzed Cross-Coupling Reactions of Organoiodides with Disulfides: Access to Aryl Sulfides and Vinyl Sulfide Derivatives DOI

Lizhu Zhang,

Yan-Fei Hu, Fen Zhao

et al.

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

Published: March 13, 2025

Thioethers and their derivatives play important roles in synthetic chemistry, medicinal materials science. Herein, we report a hemilabile P,N-ligand-assisted gold-catalyzed C-S cross-coupling reaction of organoiodides with disulfides. In this reaction, alkyl or aryl disulfides react smoothly vinyl iodides to afford series sulfide good excellent yields. The robust capabilities thioether synthesis are exemplified by the readily available easily handled reagents as well compatibility wide range functional groups.

Language: Английский

Citations

0
Chelating-Group-Assisted C(sp2)–O Reductive Elimination at the Gold(III) Center DOI
Avishek Das, Sadhana Tripathi, Lisa Roy

et al.

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

Published: May 1, 2025

Herein, we demonstrate chelating-group-assisted C(sp2)-O reductive elimination at gold(III) centers. Detailed stoichiometric studies highlighted the importance of a chelating group for achieving successful C-O elimination, paving way development catalytic version. The mechanistic investigations, including control experiments, 31P NMR, mass spectrometry, and density functional theory (DFT) studies, suggested that synergistic effect ligand creates highly coordinated environment around Au(III) center to facilitate bond-forming reaction.

Language: Английский

Citations

0