Dearomatization Approach to 2-Trifluoromethylated Benzofuran and Dihydrobenzofuran Products

David T. Smith, Edon Vitaku, Jon T Njardarson

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

A mild dearomatization enabled ortho-selective replacement of an aromatic C-H bond with a hexafluoroacetylacetone (hfacac) substituent has been developed. This reaction is dependent on a hypervalent iodine generated phenoxonium intermediate, a critical choice of solvent, and reagent addition order. The fluorinated dihydrobenzofuran product can be transformed into dihydrobenzofuran and benzofuran products decorated with a 2-trifluoromethyl group. The 3-trifluoromethylacyl substituted benzofurans rapidly form hydrates, which can be reduced to the corresponding alcohols.

Original languageEnglish (US)
Pages (from-to)3508-3511
Number of pages4
JournalOrganic Letters
Volume19
Issue number13
DOIs
StatePublished - Jul 7 2017

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Benzofurans
Hydrates
Iodine
Alcohols
products
hydrates
iodine
reagents
alcohols
benzofuran

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Dearomatization Approach to 2-Trifluoromethylated Benzofuran and Dihydrobenzofuran Products. / Smith, David T.; Vitaku, Edon; Njardarson, Jon T.

In: Organic Letters, Vol. 19, No. 13, 07.07.2017, p. 3508-3511.

Research output: Contribution to journalArticle

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