An alternative to the classical α-arylation: the transfer of an intact 2-iodoaryl from ArI(O₂CCF₃)

The α-arylation of carbonyl compounds is generally accomplished under basic conditions, both under metal catalysis and via aryl transfer from the diaryl λ(3)-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 appli...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2014-10, Vol.53 (42), p.11298-11301
Main Authors: Jia, Zhiyu, Gálvez, Erik, Sebastián, Rosa María, Pleixats, Roser, Álvarez-Larena, Ángel, Martin, Eddy, Vallribera, Adelina, Shafir, Alexandr
Format: Article
Language:English
Online Access:Get full text
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Summary:The α-arylation of carbonyl compounds is generally accomplished under basic conditions, both under metal catalysis and via aryl transfer from the diaryl λ(3)-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.
ISSN:1521-3773
DOI:10.1002/anie.201405982