Redox-active esters (RAEs) as alkyl radical precursors have been extensively developed for C-C bond formations. However, the analogous transformation of fluoroalkyl radicals from the corresponding acetic acid or ester precursors remain thermal-dynamically unfavoured and operationally challenged due to the high oxidation potential of the fluoroalkylacetate anions. The newly developed N-hydroxybenzimidoyl chloride (NHBC) ester provides a general leaving group-assisted strategy to generate a portfolio of fluoroalkyl radicals, which can be successfully applied in photoinduced decarboxylative hydrofluoroalkylation and heteroarylation of unactivated olefins. In addition, DFT calculations revealed that the NHBC ester was in favor of fluorocarbon radical pathway while other well-known RAEs were in preference of the nitrogen radical pathway.

General leaving group-assisted strategy for photoinduced fluoroalkylations using N-hydroxybenzimidoyl chloride esters

2019 Spring National Meeting

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