Difluorinative ring expansions of benzo-fused carbocycles and heterocycles are achieved with p-(difluoroiodo)toluene. Issue 98 (25th November 2019)

• Record Type: Journal Article
• Authors: Zhao, Zhensheng; To, Avery J.; Murphy, Graham K.
• Is Part Of: Chemical communications. Volume 55:Issue 98(2019)
• Page Start: 14821
• Page End: 14824
• Publication Date: 2019-11-25
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c9cc08310c
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : Fluorination of exocyclic alkenes and allenes with p -TolIF2 gives ring-expanded β, β-difluorides via a 1, 2-phenyl shift. Abstract : A chemoselective fluorinative ring expansion has been realized using the hypervalent iodine (HVI) reagent p -TolIF2, which delivers β, β-difluoroalkyl arenes in yields up to 89% and allylic gem -difluorides in yields up to 78%. This rapid reaction exploits the ambiphilic nature of alkenes and allenes, and incorporates both fluorine atoms of the (difluoroiodo)arene in the products. The mechanism involves a 1, 2-phenyl shift, which provides access in one step to important fluorinated building blocks for bioactive molecule synthesis.