Electrochemical [3+3] Annulation of Phenol and Hydrazone: Synthesis of 1,3,4-Oxadiazines

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

Published: Feb. 19, 2025

A novel [3+3] cyclization reaction between phenol and hydrazone was successfully developed under electrochemically driven conditions. This provided access to a diverse array of 1,3,4-oxadiazinane compounds in consistently high yields, reaching up 87%. Notably, the exhibited remarkable tolerance toward broad spectrum both substrates, underscoring its versatility. Moreover, protocol distinguished itself by exceptional atom step economy, facilitating efficient construction functionalized 1,3,4-oxadiazines. The synthetic utility this approach further exemplified scalability, as demonstrated gram-scale reactions, substrate scope.

Language: Английский

Synthesis of Non-C₂-Symmetric Biaryldiols via Organo-Electro Catalyzed Aryl–Aryl Dehydrogenative Cross-Coupling

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: 147(9), P. 7524 - 7532

Published: Feb. 19, 2025

Despite a few successful examples, controlling the enantioselectivity in asymmetric synthesis of non-C2-symmetric biaryldiols has long been challenging. To address issues and regioselectivity, we introduced novel organoelectrocatalytic strategy enabling aryl-aryl dehydrogenative cross-coupling reactions. Using this approach, valuable were obtained up to 95% yields 97% enantiomeric excesses (ees), these compounds could be further applied as versatile ligands Detailed mechanistic studies supported sequential diradical followed by central-to-axial chirality conversion pathway.

Language: Английский