An Alternative to the Classical α-Arylation: The Transfer of an Intact 2-Iodoaryl from ArI(O2CCF3)2

Zhiyu Jia, Erik Gálvez, Rosa María Sebastián, Roser Pleixats, Ángel Álvarez-Larena, Eddy Martin, Adelina Vallribera, Alexandr Shafir

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63 Citations (Scopus)

Abstract

© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. The α-arylation of carbonyl compounds is generally accomplished under basic conditions, both under metal catalysis and via aryl transfer from the diaryl λ3-iodanes. Here, we describe an alternative metal-free α-arylation using ArI(O2CCF3)2 as the source of a 2-iodoaryl group. The reaction is applicable to activated ketones, such as α-cyanoketones, and works with substituted aryliodanes. This formal C-H functionalization reaction is thought to proceed through a [3,3] rearrangement of an iodonium enolate. The final α-(2-iodoaryl)ketones are versatile synthetic building blocks.
Original languageEnglish
Pages (from-to)11298-11301
JournalAngewandte Chemie - International Edition
Volume53
Issue number42
DOIs
Publication statusPublished - 1 Oct 2014

Keywords

  • C-H functionalization
  • dehydrogenative C-C coupling
  • hypervalent iodine
  • iodonium-Claisen rearrangement
  • α-arylation

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