Hypervalent-Iodine-Mediated Ring-Contraction Monofluorination Affording Monofluorinated Five-Membered Ring-Fused Oxazolines.

Abstract

The first ring-contraction monofluorination reaction mediated by a hypervalent iodine reagent is reported, and the use of the reaction for the synthesis of monofluorinated five-membered ring-fused oxazolines is described. By means of this reaction, a fluorine atom can be selectively introduced either on the five-membered ring or external to it, depending on whether or not the substrate has C-4 alkyl substituents. The reaction was used for the further conversion of probenecid and isoxepac.

DOI: 10.1021/acs.orglett.7b02479

Cite this paper

@article{Han2017HypervalentIodineMediatedRM, title={Hypervalent-Iodine-Mediated Ring-Contraction Monofluorination Affording Monofluorinated Five-Membered Ring-Fused Oxazolines.}, author={Yong-Chao Han and Yan-dong Zhang and Qun Jia and Jian Cui and Chi Zhang}, journal={Organic letters}, year={2017}, volume={19 19}, pages={5300-5303} }