Synthesis of highly substituted fluorenones via metal-free TBHP-promoted oxidative cyclization of 2-(aminomethyl)biphenyls. Application to the total synthesis of nobilone

Highly substituted fluorenones are readily prepared in mostly fair to good yields via metal- and additive-free TBHP-promoted cross-dehydrogenative coupling (CDC) of readily accessible -methyl-2-(aminomethyl)biphenyls and 2-(aminomethyl)biphenyls. This methodology is compatible with numerous function...

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Bibliographic Details
Published inBeilstein journal of organic chemistry Vol. 17; no. 1; pp. 2668 - 2679
Main Authors Jourjine, Ilya A P, Zeisel, Lukas, Krauß, Jürgen, Bracher, Franz
Format Journal Article
LanguageEnglish
Published Germany Beilstein-Institut 02.11.2021
Subjects
Chemistry
cross-dehydrogenative coupling
cyclization
fluorenones
Full Research Paper
nobilone
total synthesis
nobilone
total synthesis
cyclization
fluorenones
cross-dehydrogenative coupling
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Summary:Highly substituted fluorenones are readily prepared in mostly fair to good yields via metal- and additive-free TBHP-promoted cross-dehydrogenative coupling (CDC) of readily accessible -methyl-2-(aminomethyl)biphenyls and 2-(aminomethyl)biphenyls. This methodology is compatible with numerous functional groups (methoxy, cyano, nitro, chloro, and SEM and TBS-protective groups for phenols) and was further utilized in the first total synthesis of the natural product nobilone.
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ISSN:1860-5397
1860-5397
DOI:10.3762/bjoc.17.181