title: An alternative to the classical α-arylation: the transfer of an intact 2-iodoaryl from ArI(O₂CCF₃)₂.
abstract: 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.
authors.affiliation: Department of Chemistry and Centro de Innovación en Química Avanzada (ORFEO-CINQA), Universitat Autònoma de Barcelona, Bellaterra (Spain).
authors.forename: Zhiyu
authors.initials: Z
authors.lastname: Jia
authors.forename: Erik
authors.initials: E
authors.lastname: Gálvez
authors.forename: Rosa María
authors.initials: RM
authors.lastname: Sebastián
authors.forename: Roser
authors.initials: R
authors.lastname: Pleixats
authors.forename: Ángel
authors.initials: Á
authors.lastname: Álvarez-Larena
authors.forename: Eddy
authors.initials: E
authors.lastname: Martin
authors.forename: Adelina
authors.initials: A
authors.lastname: Vallribera
authors.forename: Alexandr
authors.initials: A
authors.lastname: Shafir
keywords: CH functionalization; dehydrogenative CC coupling; hypervalent iodine; iodonium-Claisen rearrangement; α-arylation