Regioselective Transition-Metal-Free Oxidative Cyclobutanol Ring Expansion to 4‑Tetralones

A facile and transition-metal-free ring expansion of the cyclobutanol moiety to 4-tetralones fused to heteroaromatic systems is described. The oxidative ring expansion proceeds rapidly and regioselectively through mediation by N-bromosuccinimide and acetonitrile in satisfactory to good yields. The p...

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Bibliographic Details
Published inOrganic letters Vol. 20; no. 24; pp. 8030 - 8034
Main Authors Natho, Philipp, Kapun, Mia, Allen, Lewis A. T, Parsons, Philip J
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 21.12.2018
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
KETONES
OPENING FUNCTIONALIZATION
REGIOSPECIFIC SYNTHESIS
MIGRATION SEQUENCES
CLEAVAGE
STRATEGY
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Summary:A facile and transition-metal-free ring expansion of the cyclobutanol moiety to 4-tetralones fused to heteroaromatic systems is described. The oxidative ring expansion proceeds rapidly and regioselectively through mediation by N-bromosuccinimide and acetonitrile in satisfactory to good yields. The preparation of precursors and the ring expansion have proven to be scalable and are straightforward to carry out.
Bibliography:UKRI
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b03619