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An Alternative to the Classical α‐Arylation: The Transfer of an Intact 2‐Iodoaryl from ArI(O 2 CCF 3 ) 2
Author(s) -
Jia Zhiyu,
Gálvez Erik,
Sebastián Rosa María,
Pleixats Roser,
ÁlvarezLarena Ángel,
Martin Eddy,
Vallribera Adelina,
Shafir Alexandr
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201405982
Subject(s) - catalysis , chemistry , aryl , combinatorial chemistry , surface modification , metal , transfer (computing) , computational chemistry , organic chemistry , computer science , parallel computing , alkyl
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(O 2 CCF 3 ) 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 CH 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.