An Alternative to the Classical α‐Arylation: The Transfer of an Intact 2‐Iodoaryl from ArI(O2CCF3)21. Issue 42 (4th September 2014)

• Record Type: Journal Article
• Authors: Jia, Zhiyu; Gálvez, Erik; Sebastián, Rosa María; Pleixats, Roser; Álvarez‐Larena, Ángel; Martin, Eddy; Vallribera, Adelina; Shafir, Alexandr
• Is Part Of: Angewandte Chemie international edition. Volume 53:Issue 42(2014)
• Page Start: 11298
• Page End: 11301
• Publication Date: 2014-09-04
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201405982
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>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.</p> </abstract>