Mechanistic Insights from Density Functional Theory into Rh/Acid-Catalyzed Synthesis of 1,2-Dihydroquinolines via Skeleton-Reorganizing Coupling of Cycloheptatriene and Amines

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(17), P. 12514 - 12523

Published: Aug. 27, 2024

Density functional theory calculations were conducted to refine our understanding at the molecular level of synthesis fused 1,2-dihydroquinolines through Rh- and acid-catalyzed skeleton-reorganizing coupling reactions cycloheptatriene with amines. The results reveal that reaction progresses via cascade catalysis, consisting consecutive steps Rh-catalyzed intermolecular involving two Rh

Language: Английский

Terpenylation of Ketones and a Secondary Alcohol under Hydrogen-Borrowing Manganese Catalysis

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

Published: Dec. 16, 2024

An Earth-abundant Mn-PNP pincer complex-catalyzed terpenylation of cyclic and acyclic ketones secondary alcohol 1-phenylethanol using isoprenoid derivatives prenol, nerol, phytol, solanesol, E-farnesol as allyl surrogates is reported. The C-C coupling reactions are green atom-economic, proceeding via dehydrogenation alcohols following a hydrogen autotransfer methodology aided by metal-ligand cooperation.

Language: Английский