Regioselective synthesis of 1- and 4-tetralones from heteroaryl-3-cyclobutanols

Herein we describe the first transition-metal-free ring expansion of four-membered rings to 1-tetralones from 3-substituted heteroaromatic compounds, and the first example of an oxetanol ring expansion to an oxa-tetralone. We also experimentally investigate the mechanism of the silver-mediated ring...

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Bibliographic Details
Published in:Tetrahedron 2020-11, Vol.76 (47), p.131636, Article 131636
Main Authors: Natho, Philipp, Rouse, Annie B., Greenfield, Jake L., Allen, Lewis A.T., White, Andrew J.P., Yang, Zeyu, Parsons, Philip J.
Format: Article
Language:English
Subjects:
Cyclic voltammetry
Cyclobutanols
Divergent synthesis
Heteroaromatics
Ring expansion
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Summary:Herein we describe the first transition-metal-free ring expansion of four-membered rings to 1-tetralones from 3-substituted heteroaromatic compounds, and the first example of an oxetanol ring expansion to an oxa-tetralone. We also experimentally investigate the mechanism of the silver-mediated ring expansion and elucidate the active oxidant in these systems using electrochemical techniques. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2020.131636