Organic Letters
Organic Letters
5 years ago

Synthesis of π-Extended Fluoranthenes via a KHMDS-Promoted Anionic-Radical Reaction Cascade

Synthesis of π-Extended Fluoranthenes via a KHMDS-Promoted Anionic-Radical Reaction Cascade
Ken-ichi Yamada, Yousuke Yamaoka, Kiyosei Takasu, Naoki Ogawa
An unprecedented KHMDS-promoted domino reaction to furnish hydroxyfluoranthenes is described. Biaryl compounds bearing acyl and naphthylalkenyl moieties are transformed into 9-hydroxydibenzo[j,l]fluoranthenes in a single step through the formation of an aromatic and a pentagonal ring system. A variety of fluoranthenes including those with extended π-conjugation, a heteroaromatic ring, and unsymmetrical substituents could be synthesized. Mechanistic studies reveal a unique reaction cascade where KHMDS acts as both a base and a single-electron donor.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01538

DOI: 10.1021/acs.orglett.7b01538

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