Supranovich Vyacheslav I, Dmitriev Igor A, Dilman Alexander D
N. D. Zelinsky Institute of Organic Chemistry, 119991 Moscow, Leninsky prosp. 47, Russian Federation.
Moscow State University, Department of Chemistry, 119991, Moscow, Leninskie Gory 1-3, Russian Federation.
Beilstein J Org Chem. 2020 Dec 29;16:3104-3108. doi: 10.3762/bjoc.16.260. eCollection 2020.
A method for the one-step construction of 3,3,4,4-tetrafluorinated piperidines from nitrones and readily accessible tetrafluorinated iodobromobutane is described. The reaction requires an excess amount of ascorbic acid as the terminal reductant and is performed in the presence of an iridium photocatalyst activated by blue light. The annelation is a result of a radical addition at the nitrone, intramolecular nucleophilic substitution, and reduction of the N-O bond.
描述了一种由硝酮和易于获得的四氟碘溴丁烷一步构建3,3,4,4-四氟哌啶的方法。该反应需要过量的抗坏血酸作为末端还原剂，并在蓝光激活的铱光催化剂存在下进行。环化反应是硝酮处的自由基加成、分子内亲核取代以及N-O键还原的结果。
