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

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

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(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

6
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
Catalytic Transfer Hydrodeoxygenation of Lignin-Derived Phenolic Compounds over RuMo/NC with Isopropanol as In Situ Hydrogen Source DOI
Dong Luo, Xin Gao, Ping Lu

et al.

Energy & Fuels, Journal Year: 2025, Volume and Issue: unknown

Published: April 22, 2025

Language: Английский

Citations

0
Gold-Catalyzed Migratory Insertion of Alkynes DOI
Avishek Das,

Biswajit Biswas,

Vincent Gandon

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 7867 - 7876

Published: April 28, 2025

Language: Английский

Citations

0
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

1
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