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Synthesis of Spirocyclic Diarylfluorenes by One-Pot Twofold SNAr Reactions of Diaryl Sulfones with Diarylmethanes

Author:
Bhanuchandra, M., Yorimitsu, Hideki, Osuka, Atsuhiro
Source:
Organic letters 2016 v.18 no.3 pp. 384-387
ISSN:
1523-7052
Subject:
chemical reactions, chemical structure, organic compounds
Abstract:
Treatment of dibenzothiophene dioxides with cyclic diarylmethanes in the presence of KN(SiMe₃)₂ results in the formation of fluorene-based spirocyclic tetraarylmethanes in a single operation. The transformation would proceed via an intermolecular SNAr reaction of the dioxides with cyclic diarylmethylpotassium followed by intramolecular SNAr cyclization. This straightforward strategy provides a wide range of spirocyclic diarylfluorenes including unusual ones that are otherwise difficult to synthesize.
Agid:
5792267