Details

Autor(en) / Beteiligte

• Deng, Ruixian
• Zhan, Shuming
• Li, Chunyu
• Gu, Zhenhua

Titel

Hypervalent‐Iodine‐Mediated Carbon–Carbon Bond Cleavage and Dearomatization of 9H‐Fluoren‐9‐ols

Ist Teil von

• Angewandte Chemie International Edition, 2020-02, Vol.59 (8), p.3093-3098

Auflage

International ed. in English

Ort / Verlag

Germany: Wiley Subscription Services, Inc

Erscheinungsjahr

2020

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• A transition‐metal‐free synthesis of spiro compounds from 9H‐fluoren‐9‐ols mediated by hypervalent iodine is reported. In this reaction, an unprecedented β‐carbon elimination of tertiary alkoxyliodine(III) to form new diaryliodonium salts is proposed. The obtained phenol intermediates undergo oxidative dearomatization to furnish a class of oxo‐spiro compounds. This domino reaction significantly increases the complexity of these molecules and shows excellent regio‐ and stereoselectivity. The best things come with iodine(III): A carbon–carbon bond cleavage reaction of 9H‐fluoren‐9‐ols mediated by hypervalent iodine(III) is reported. The reaction continues with reductive elimination and dearomatization. A class of spiro compounds were synthesized in a highly efficient and stereoselective manner.