Jump to main content
Jump to site search

Issue 98, 2019
Previous Article Next Article

Difluorinative ring expansions of benzo-fused carbocycles and heterocycles are achieved with p-(difluoroiodo)toluene

Author affiliations

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.

Graphical abstract: Difluorinative ring expansions of benzo-fused carbocycles and heterocycles are achieved with p-(difluoroiodo)toluene

Back to tab navigation

Supplementary files

Publication details

The article was received on 23 Oct 2019, accepted on 18 Nov 2019 and first published on 18 Nov 2019


Article type: Communication
DOI: 10.1039/C9CC08310C
Chem. Commun., 2019,55, 14821-14824

  •   Request permissions

    Difluorinative ring expansions of benzo-fused carbocycles and heterocycles are achieved with p-(difluoroiodo)toluene

    Z. Zhao, A. J. To and G. K. Murphy, Chem. Commun., 2019, 55, 14821
    DOI: 10.1039/C9CC08310C

Search articles by author

Spotlight

Advertisements