Copper‐Catalyzed Three‐Component Selective 1,4‐Amino Oxygenation of 1,3‐Dienes
Year: 2025
Type: article
Abstract: Multicomponent difunctionalization of 1,3‐dienes has emerged as a promising strategy for rapid synthesis of valuable allylic compounds. Here, we report an unprecedented three‐component 1,4‐amino oxygenation of 1,3‐dienes, enabled by copper catalysis and strong Brønsted acid. The reaction engages a novel mechanism that merges umpolung electrophilic amination via copper(I)‐catalyzed formation of aminium radical cations and copper (II)‐mediated carbon‐oxygen bond formation with alcohols. The observed 1,4‐selectivity is modulated by noncovalent interactions of aminated allylic intermediates. This method presents broad synthetic utility and offers a rapid entry to ( E )‐1,4‐allylic amino ethers, which can be derivatized into various polyfunctional molecules with high stereocontrol.
Source: Angewandte Chemie
Authors: Guangshou Feng, Maria K. Velopolcek, Qiu Wang
Institution: Duke University
Language: German
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $5,790
OpenAlex ID: W7117353602