Regioselective pyridazine synthesis from tetrazines and alkynyl sulfides DOI Creative Commons
Chika Yamamoto,

Koyo Numata,

Minori Suzuki

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(21), P. 6159 - 6165

Published: Jan. 1, 2024

A regioselective synthesis of trisubstituted pyridazines from tetrazines and alkynyl sulfides is disclosed. Good transformability sulfur-substituents allowed us to synthesize various pyridazines.

Language: Английский

Zwitterionic Dual Halogen Bond-Catalyzed Electrophilic Bromination of Electron-Deficient Arenes under Mild Conditions DOI
Muyin Zhang, Zhihai Ke

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 4270 - 4279

Published: Feb. 25, 2025

Language: Английский

Citations

2
HFIP-Promoted Aromatic Electrophilic Amidation of Indoles and Pyrroles with Isocyanates DOI
Liang-Bi Chen, Decheng Li, Hongye Wang

et al.

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

Published: March 19, 2025

A mild and practical method for synthesizing amidoindoles amidopyrroles was described via the direct amidation of indoles or pyrroles with isocyanates promoted by 1,1,1,3,3,3-hexafluoroisopropanol (HFIP). In this reaction, HFIP acted as a strong hydrogen bond-donating solvent to activate isocyanates, enabling electron-rich nitrogen-containing heterocycles.

Language: Английский

Citations

0
Triflic Acid-Mediated Chemoselective Indole C2-Heteroarylation of Peptide Tryptophan Residues by Triazine DOI
Jian Li, Qi-Long Hu,

Jia-Shu Liu

et al.

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

Published: Dec. 9, 2024

Peptide modification provides opportunities to afford peptides with designed functions. Among the proteogenic amino acids, tryptophan represents an ideal and attractive target for peptide because of exclusive chemical reactivity its unique indole structure. Herein, we reported C2 position-selective transition-metal-free approach derivatives tryptophan-containing by triazine via triflic acid activation that incorporated functional group could act as orthogonal handle further bioconjugation inverse electron demand Diels–Alder reaction.

Language: Английский

Citations

1
Unraveling Alcohol Additive Effects on Hypervalent Iodine(III)-Catalyzed Asymmetric Phenolic Dearomatization: Ligand Substitution and Low-Barrier Hydrogen Bonds DOI
Hanliang Zheng, Cai Liu,

Xiaoyu Lai

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 15(1), P. 370 - 380

Published: Dec. 18, 2024

Despite the widespread use of hexafluoropropanol (HFIP) as a "magic" solvent or additive in organic synthesis, its fundamental mechanisms lag far behind. This study presents mechanistic insights into puzzling alcohol effects observed Ishihara's conformationally flexible C2-symmetric iodoarene-catalyzed asymmetric phenolic dearomatization through density functional theory calculations. The results reveal that due to "booster effect" fluorinated alcohols, HFIP assembles trimeric hydrogen bond cluster displaces ligand from active iodine(III) catalyst and forms low-barrier with substrate, which significantly enhances oxidizing power center, thus facilitating electron-deficient phenols. Conversely, methanol is found promote electron-rich phenols via formally similar yet distinct mechanism, highlighting unique role an additive. gained this investigation advance our molecular-level understanding synergistic interactions between catalysts additives, potentially guiding design catalytic systems exploit these for broader applications.

Language: Английский

Citations

1
The inverse electron demand diels-alder (IEDDA): A facile bioorthogonal click reaction for development of injectable polysaccharide-based hydrogels for biomedical applications DOI
Lihua Yan, Zhenzhen Zhao, Yuqian Liu

et al.

Carbohydrate Polymers, Journal Year: 2024, Volume and Issue: 352, P. 123142 - 123142

Published: Dec. 16, 2024

Language: Английский

Citations

0
Regioselective pyridazine synthesis from tetrazines and alkynyl sulfides DOI Creative Commons
Chika Yamamoto,

Koyo Numata,

Minori Suzuki

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(21), P. 6159 - 6165

Published: Jan. 1, 2024

A regioselective synthesis of trisubstituted pyridazines from tetrazines and alkynyl sulfides is disclosed. Good transformability sulfur-substituents allowed us to synthesize various pyridazines.

Language: Английский

Citations

0