Angew Chem Int Ed Engl
State Key Laboratory of Elemento-Organic Chemistry, The Research Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, 94 Weijin Road, Tianjin, 300071, China.
Published: November 2021
Herein, we report a new strategy for carbon-carbon bond scission and intramolecular ring expansion fluorination of unactivated cyclopropanes, which was accomplished with a new hypervalent fluoroiodane(III) reagent 1. This novel method delivers medicinally relevant 4-fully substituted fluoropiperidines in moderate to high yields with excellent regio- and diastereoselectivity. Reagent 1, which has an N-acetylbenziodazole framework, was readily synthesized via three steps in 76 % overall yield and was characterized by NMR spectroscopy and X-ray crystallography. Owing to the presence of a secondary I⋅⋅⋅O bonding interaction between the λ -iodane atom and the carbonyl oxygen of the acetyl group of the N-acetylbenziodazole framework, 1 has excellent stability and can be stored at ambient temperature for 6 months without any detectable decomposition. Density functional theory calculations and experimental studies showed that the reaction proceeds via a carbocation intermediate that readily combines with a fluoride ion to generate the product.
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