Discovery and Mechanistic Study of a Totally Organic C(aryl)–C(alkyl)Oxygen Insertion Reaction

Discovery and Mechanistic Study of a Totally Organic C(aryl)–C(alkyl)Oxygen Insertion Reaction

We report an unprecedented photochemical oxygen insertion reaction into an aromatic quinone methide. Insertion happens specifically within a C(aryl)–C(alkyl) bond, whereas the quinone methide moiety remains intact itself. Detailed mechanistic studies, supported by DFT calculations, support a pathway...

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Veröffentlicht in:Journal of organic chemistry 2019-11, Vol.84 (21), p.14349-14353
Hauptverfasser: Kazim, Muhammad, Foy, Hayden, Siegler, Maxime A, Dudding, Travis, Lectka, Thomas
Format: Artikel
Sprache:eng
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Zusammenfassung:We report an unprecedented photochemical oxygen insertion reaction into an aromatic quinone methide. Insertion happens specifically within a C(aryl)–C(alkyl) bond, whereas the quinone methide moiety remains intact itself. Detailed mechanistic studies, supported by DFT calculations, support a pathway in which the p-QM plays a pivotal activating role.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b02238