4‐Chloro‐2‐azaadamantane N‐Oxyl (4‐Cl‐AZADO): A Readily Preparable Organocatalyst for NOx Co‐catalyzed Aerobic Alcohol Oxidation. Issue 4 (17th February 2023)

• Record Type: Journal Article
• Authors: Nagasawa, Shota; Sasano, Yusuke; Iwabuchi, Yoshiharu
• Is Part Of: Asian journal of organic chemistry. Volume 12:Issue 4(2023)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2023-02-17
• Subjects: Alcohol -- Organocatalysis -- Oxidation -- Radicals -- Synthetic method; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.202300031
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: Concise synthesis and structure‐activity relationships study of 4‐substituted 2‐azaadamantane N ‐oxyls reveals that 4‐chloro‐2‐azaadamantane N ‐oxyl (4‐Cl‐AZADO) is an efficient organocatalyst toward the aerobic oxidation of alcohols in the presence of NOx as a co‐catalyst. The organocatalyst was easily synthesized from 2‐adamantanone in five steps, and it showed high activity compared with many previously reported nitroxyl radical catalysts. Abstract : 4‐chloro‐2‐azaadamantane N ‐oxyl (4‐Cl‐AZADO) enabled upon coupling with NOx an efficient, transition‐metal‐free aerobic oxidation of alcohols. 4‐Cl‐AZADO is easily preparable in multigram‐scale and posesses high catalytic activity compared with many previously reported nitroxyl radical catalysts.