Transition Metal-Free Direct C–H Functionalization of Quinones and Naphthoquinones with Diaryliodonium Salts: Synthesis of Aryl Naphthoquinones as β‑Secretase Inhibitors

A novel ligand-free, transition metal-free direct C–H functionalization of quinones with diaryliodonium salts has been developed for the first time. The transformation was promoted only through the use of a base and gave aryl quinone derivatives in moderate to good yields. This methodology provided...

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Veröffentlicht in:Journal of organic chemistry 2014-09, Vol.79 (18), p.8607-8613
Hauptverfasser: Wang, Dawei, Ge, Bingyang, Li, Liang, Shan, Jie, Ding, Yuqiang
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Sprache:eng
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Zusammenfassung:A novel ligand-free, transition metal-free direct C–H functionalization of quinones with diaryliodonium salts has been developed for the first time. The transformation was promoted only through the use of a base and gave aryl quinone derivatives in moderate to good yields. This methodology provided an effective and easy way to synthesize β-secretase inhibitors. The radical trapping experiments showed that this progress was the radical mechanism.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo501467v