4.7 Article

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

期刊

CHEMICAL COMMUNICATIONS
卷 55, 期 98, 页码 14821-14824

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ROYAL SOC CHEMISTRY
DOI: 10.1039/c9cc08310c

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  1. Natural Sciences and Engineering Research Council (NSERC) of Canada
  2. University of Waterloo
  3. Province of Ontario

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A chemoselective fluorinative ring expansion has been realized using the hypervalent iodine (HVI) reagent p-TolIF(2), which delivers beta,beta-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.

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