Open AccessFacile Oxidative Rearrangements Using Hypervalent Iodine Reagents
Author(s) -
Singh Fateh V.,
Rehbein Julia,
Wirth Thomas
Publication year - 2012
Publication title -
chemistryopen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.644
H-Index - 29
ISSN - 2191-1363
DOI - 10.1002/open.201200037
Subject(s) - hypervalent molecule , iodine , reagent , chemistry , cationic polymerization , iodine compounds , combinatorial chemistry , ring (chemistry) , oxidative phosphorylation , organic chemistry , biochemistry
Aromatic substituents migrate in a novel oxidative cyclization mediated by iodine(III) reagents. 4‐Arylbut‐3‐enoic acids are cyclized and rearranged to 4‐arylfuran‐2(5 H )‐ones by hypervalent iodine compounds in good to excellent yields under mild reaction conditions. Other ring sizes are also accessible. The mechanism of the reaction is described in detail, and calculations highlight the cationic nature of the intermediates in the rearrangement. The fast access to heavily substituted furanones is used for the synthesis of biologically active derivatives.