Transition-Metal-Free Access to Heteroaromatic-Fused 4‑Tetralones by the Oxidative Ring Expansion of the Cyclobutanol Moiety

Advances in the transition-metal-free cyclobutanol ring expansion to 4-tetralones under N-bromosuccinimide mediation are described. We have expanded the scope of this ring expansion methodology and investigated the effect substituents on the aromatic ring, and the cyclobutanol moiety, have on the ou...

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Bibliographic Details
Published in:Journal of organic chemistry 2019-08, Vol.84 (15), p.9611-9626
Main Authors: Natho, Philipp, Allen, Lewis A. T, White, Andrew J. P, Parsons, Philip J
Format: Article
Language:English
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Summary:Advances in the transition-metal-free cyclobutanol ring expansion to 4-tetralones under N-bromosuccinimide mediation are described. We have expanded the scope of this ring expansion methodology and investigated the effect substituents on the aromatic ring, and the cyclobutanol moiety, have on the outcome of the reaction. Limitations with certain substituents on the cyclobutanol moiety are also described. Further experimental evidence to support our mechanistic understanding is disclosed, and we now preclude the suggested involvement of a primary radical for this transformation.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b01290