13314-98-2Relevant academic research and scientific papers
Electrochemical Generation of Hypervalent Bromine(III) Compounds
Francke, Robert,Mohebbati, Nayereh,Sokolovs, Igors,Suna, Edgars
supporting information, p. 15832 - 15837 (2021/06/14)
In sharp contrast to hypervalent iodine(III) compounds, the isoelectronic bromine(III) counterparts have been little studied to date. This knowledge gap is mainly attributed to the difficult-to-control reactivity of λ3-bromanes as well as to their challenging preparation from the highly toxic and corrosive BrF3 precursor. In this context, we present a straightforward and scalable approach to chelation-stabilized λ3-bromanes by anodic oxidation of parent aryl bromides possessing two coordinating hexafluoro-2-hydroxypropanyl substituents. A series of para-substituted λ3-bromanes with remarkably high redox potentials spanning a range from 1.86 V to 2.60 V vs. Ag/AgNO3 was synthesized by the electrochemical method. We demonstrate that the intrinsic reactivity of the bench-stable bromine(III) species can be unlocked by addition of a Lewis or a Br?nsted acid. The synthetic utility of the λ3-bromane activation is exemplified by oxidative C?C, C?N, and C?O bond forming reactions.
KI-catalyzed imidation of sp3 C-H bond adjacent to amide nitrogen atom
Lao, Zhi-Qi,Zhong, Wen-He,Lou, Qing-Hua,Li, Zhong-Jun,Meng, Xiang-Bao
supporting information, p. 7869 - 7871 (2013/07/05)
We have developed a new KI-catalyzed method for the imidation of an sp 3 C-H bond adjacent to an amide nitrogen atom by using TBHP (tert-butyl hydroperoxide, 70% aqueous solution) as the oxidant. This novel procedure tolerated air and moisture and provided a series of novel products in moderate to excellent yields under mild conditions.
