214603-19-7Relevant articles and documents
Evolution of N-Heterocycle-Substituted Iodoarenes (NHIAs) to Efficient Organocatalysts in Iodine(I/III)-Mediated Oxidative Transformations
Boelke, Andreas,Nachtsheim, Boris J.
supporting information, p. 184 - 191 (2019/12/11)
The reactivity of ortho-functionalized N-heterocycle-substituted iodoarenes (NHIAs) as organocatalysts in iodine(I/III)-mediated oxidations was systematically investigated in the α-tosyloxylation of ketones as the model reaction. During a systematic catalyst evolution, it was found that NH-triazoles and benzoxazoles have the most significant positive influence on the reactivity of the central iodine atom. A further catalyst improvement which focused on the substitution pattern of the arene revealed a remarkable ortho-effect. By introduction of an o-OMe group we were able to generate a novel NHIA with a so far unseen catalytic efficiency. This new catalyst is not only easy to synthesize but also enabled the α-tosyloxylation of carbonyl compounds at the lowest reported catalyst loading of only 1 mol%. Finally, the performance of this iodine(I) catalyst was successfully demonstrated in intramolecular oxidative couplings of biphenyls and oxidative rearrangements. (Figure presented.).
Novel α-tosyloxylation of ketones catalyzed by the in situ generated hypoiodous acid from alkyl iodide
Zhang, Bijun,Han, Liuquan,Hu, Jiantao,Yan, Jie
, p. 5851 - 5854 (2015/01/16)
Using a catalytic amount of 1-iodopropane, a novel and efficient procedure has been developed for direct preparation of α-tosyloxyketones from ketones. In this protocol, 1-iodopropane is first oxidized into iodosylpropane, which decomposes to form the key
A facile synthesis of novel dihydroindeno[1,2-e][1,2,4]triazolo[3,4-b][1,3, 4]thiadiazines using HTIB
Prakash, Om,Aneja, Deepak Kumar,Wadhwa, Deepak,Kumar, Ravi,Arora, Sanjiv
experimental part, p. 566 - 570 (2012/08/27)
The synthesis of a series of 21 novel 3-alkyl/aryl-7/9-methyl-10,10a- dihydroindeno[1,2-e][1,2,4]triazolo[3,4-b][1,3,4]thiadiazines (4) has been achieved by the cyclocondensation between 4/6-methyl-2-tosyloxy-1-indanones (2) and 3-alkyl/aryl-4-amino-5-mercapto-1,2,4-s-triazoles (3). 4/6-Methyl-2- tosyloxy-1-indanones (2) were readily accessible through hypervalent iodine oxidation of 4/6-methyl-1-indanones using [(hydroxy)tosyloxyiodo]benzene (HTIB, Koser's reagent) in acetonitrile.