1914-21-2Relevant articles and documents
Electrochemical behavior of N-oxyphthalimides: Cascades initiating self-sustaining catalytic reductive N―O bond cleavage
Syroeshkin, Mikhail A.,Krylov, Igor B.,Hughes, Audrey M.,Alabugin, Igor V.,Nasybullina, Darya V.,Sharipov, Mikhail Yu.,Gultyai, Vadim P.,Terent'ev, Alexander O.
, (2017)
N-oxyphthalimides are stable and easily accessible compounds that can produce oxygen radicals upon 1-electron reduction. We present a systematic study of electrochemical properties of N-oxyphthalimide derivatives (PI-ORs) in DMF by cyclic voltammetry. In all cases, electron transfer to the substrate leads to decomposition of the intermediate radical anion via the N―O bond cleavage. In the case of benzyloxyphthalimide or its derivatives containing electron-donating substituents, reductive electron transfer induces the chain decomposition of the substrate to phthalimide (PI) radical-anion and the corresponding carbonyl compound. The PI radical-anion product is a powerful reductant that can transfer an electron to the reactant PI-OR, thus establishing a catalytic cycle for reductive N―O scission. This self-catalytic process is reflected in a considerable decrease in the reduction current for the substrate (-/molecule). By contrast, reductive fragmentations of benzyl derivatives containing electron-withdrawing substituents in the aromatic ring or at the benzylic position, as well as tosyl and alkyl derivatives, occur via a 1-electron mechanism. A sequence of N―O and C―C scissions was engineered to support the intermediacy of O-centered radicals in these processes.
Preparation of cyclic imides from alkene-tethered amides: Application of homogeneous Cu(ii) catalytic systems
Chen, Suqing,Liu, Zhenghui,Mu, Tiancheng,Ou, Hualin,Tan, Xingxing,Wang, Peng,Yan, Zhenzhong,Yu, Dongkun,Zhao, Xinhui
, p. 7698 - 7707 (2020/03/13)
A Cu-based homogeneous catalytic system was proposed for the preparation of imides from alkene-tethered amides. Here, O2 acted as a terminal oxidant and a cheap and easily available oxygen source. The cleavage of CC bonds and the formation of C
Rhodium(iii)-catalyzed directed amidation of unactivated C(sp3)-H bonds to afford 1,2-amino alcohol derivatives
Dong, Yi,Chen, Jiajing,Xu, Heng
supporting information, p. 11096 - 11099 (2018/11/21)
A rhodium-catalyzed directed C(sp3)-H amidation to afford 1,2-amino alcohol oxime derivatives has been developed with good yields and a broad substrate scope. In previous methods for this type of reaction, 1-arylethan-1-ol oxime analogues were
