Regioselective Rearrangement of 4,4-Disubstituted 2-Hydroxycyclohexa-2,5-Dienones under Deoxyfluorination Conditions

Keita Takubo, Ahmed Mohamed, Takafumi Ide, Kazuyuki Saito, Takashi Ikawa, Takehiko Yoshimitsu, Shuji Akai

Research output: Contribution to journalArticle

Abstract

The dienone-phenol rearrangement is a useful tool for the synthesis of highly substituted phenols. In our previous study of the rearrangement of 4,4-disubstituted 2-hydroxycyclohexa-2,5-dienone under deoxyfluorination conditions, bond migration proceeded with very poor regioselectivity. In this paper, an acid-mediated rearrangement of O-perfluoroalkylsulfonyl difluorides with regioselective migration toward the β′-carbon is reported. This method allowed the synthesis of a fluorinated analog of allocolchicinoids with improved total yield. Successful application to other substrates was also demonstrated.

Original languageEnglish
Pages (from-to)13141-13151
Number of pages11
JournalJournal of Organic Chemistry
Volume82
Issue number24
DOIs
Publication statusPublished - Dec 15 2017
Externally publishedYes

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Regioselectivity
Phenols
Phenol
Carbon
Acids
Substrates

ASJC Scopus subject areas

  • Organic Chemistry

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Regioselective Rearrangement of 4,4-Disubstituted 2-Hydroxycyclohexa-2,5-Dienones under Deoxyfluorination Conditions. / Takubo, Keita; Mohamed, Ahmed; Ide, Takafumi; Saito, Kazuyuki; Ikawa, Takashi; Yoshimitsu, Takehiko; Akai, Shuji.

In: Journal of Organic Chemistry, Vol. 82, No. 24, 15.12.2017, p. 13141-13151.

Research output: Contribution to journalArticle

Takubo, Keita ; Mohamed, Ahmed ; Ide, Takafumi ; Saito, Kazuyuki ; Ikawa, Takashi ; Yoshimitsu, Takehiko ; Akai, Shuji. / Regioselective Rearrangement of 4,4-Disubstituted 2-Hydroxycyclohexa-2,5-Dienones under Deoxyfluorination Conditions. In: Journal of Organic Chemistry. 2017 ; Vol. 82, No. 24. pp. 13141-13151.
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