Synthesis of Benzo-Fused Cyclic Ketones via Metal-Free Ring Expansion of Cyclopropanols Enabled by Proton-Coupled Electron Transfer

The metal-free ring expansion of cyclopropanols containing a pendant styrene moiety was successfully achieved using a proton-coupled electron transfer enabled by an organic photoredox catalyst. Through this, variants of 1-tetralone and 1-benzosuberone bearing a substituent at the benzylic position w...

Full description

Saved in:
Bibliographic Details
Published inOrganic letters Vol. 23; no. 12; pp. 4710 - 4714
Main Authors Kikuchi, Tomohiro, Yamada, Keiji, Yasui, Takeshi, Yamamoto, Yoshihiko
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 18.06.2021
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Online AccessGet full text

Cover

More Information
Summary:The metal-free ring expansion of cyclopropanols containing a pendant styrene moiety was successfully achieved using a proton-coupled electron transfer enabled by an organic photoredox catalyst. Through this, variants of 1-tetralone and 1-benzosuberone bearing a substituent at the benzylic position were selectively obtained through the regioselective ring closure of alkyl radical intermediates depending on the substitution pattern of the alkene moiety.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c01436