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Hypervalent‐Iodine‐Mediated Carbon–Carbon Bond Cleavage and Dearomatization of 9 H ‐Fluoren‐9‐ols
Author(s) -
Deng Ruixian,
Zhan Shuming,
Li Chunyu,
Gu Zhenhua
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201913373
Subject(s) - hypervalent molecule , chemistry , domino , phenol , iodine , bond cleavage , stereoselectivity , medicinal chemistry , carbon fibers , molecule , cleavage (geology) , organic chemistry , catalysis , materials science , composite number , composite material , geotechnical engineering , fracture (geology) , engineering
A transition‐metal‐free synthesis of spiro compounds from 9 H ‐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.