65753-90-4Relevant articles and documents
Photoinduced Remote Functionalization of Amides and Amines Using Electrophilic Nitrogen Radicals
Morcillo, Sara P.,Dauncey, Elizabeth M.,Kim, Ji Hye,Douglas, James J.,Sheikh, Nadeem S.,Leonori, Daniele
supporting information, p. 12945 - 12949 (2018/09/14)
The selective functionalization of C(sp3)?H bonds at distal positions to functional groups is a challenging task in synthetic chemistry. Reported here is a photoinduced radical cascade strategy for the divergent functionalization of amides and protected amines. The process is based on the oxidative generation of electrophilic amidyl radicals and their subsequent transposition by 1,5-H-atom transfer, resulting in remote fluorination, chlorination and, for the first time, thioetherification, cyanation, and alkynylation. The process is tolerant of most common functional groups and delivers useful building blocks that can be further elaborated. The utility of this strategy is demonstrated through the late-stage functionalization of amino acids and a dipeptide.
Lawesson's reagent for direct thionation of hydroxamic acids: Substituent effects on LR reactivity
Przychodzen, Witold
, p. 676 - 684 (2007/10/03)
To explore the generality and scope of direct thionation of hydroxamic acids (HAs), the reaction of various structurally diverse HAs with Lawesson's reagent was investigated. The yield of thiohydroxamic acid (THAs) is poor when HAs possess bulky acyl and/or N-substituents, acidic α-hydrogen atoms, or an N-phenyl ring. THAs yields were correlated with Brown sigma parameter. The relative rates of two subsequent processes kT2 and kR2 were also measured. Correlation was also found for methine proton chemical shifts of N-isopropyl benzothiohydroxamic acids.
