1914-21-2Relevant academic research and scientific papers
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.
PCET-Based Ligand Limits Charge Recombination with an Ir(III) Photoredox Catalyst
Sayre, Hannah,Ripberger, Hunter H.,Odella, Emmanuel,Zieleniewska, Anna,Heredia, Daniel A.,Rumbles, Garry,Scholes, Gregory D.,Moore, Thomas A.,Moore, Ana L.,Knowles, Robert R.
supporting information, p. 13034 - 13043 (2021/09/03)
Upon photoinitiated electron transfer, charge recombination limits the quantum yield of photoredox reactions for which the rates for the forward reaction and back electron transfer are competitive. Taking inspiration from a proton-coupled electron transfe
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
Selective C(sp3)?H and C(sp2)?H Fluorination of Alcohols Using Practical Auxiliaries
Mao, Yang-Jie,Lou, Shao-Jie,Hao, Hong-Yan,Xu, Dan-Qian
supporting information, p. 14085 - 14089 (2018/10/15)
Selective introduction of fluorine into molecules by the cleavage of inert C?H bonds is of central academic and synthetic interest, yet remains challenging. Given the central role of alcohols in organic chemistry as the most ubiquitous building blocks, a
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
Palladium-catalyzed intermolecular amination of unactivated C(sp3)-H bonds via a cleavable directing group
Jin, Lianwen,Zeng, Xiaoli,Li, Siyang,Hong, Xuechuan,Qiu, Guofu,Liu, Peng
supporting information, p. 3986 - 3989 (2017/04/11)
Palladium-catalyzed intermolecular amination of unactivated C(sp3)-H bonds was developed. Using NFSI as both the amino source and the oxidant, this protocol operates under mild conditions with excellent terminal selectivity and a broad substrate scope. Moreover, the directing group can be easily removed to produce 1,2-amino alcohols.
High activity N - oxyl new nicotine analogs and its preparation method and application (by machine translation)
-
Paragraph 0046-0049, (2017/07/06)
The invention belongs to the insecticide field, and in particular relates to high activity N - oxyl anabasine analogue and its preparation method and application. The invention by introducing the flexible side chain, has offered a kind of novel structure, pesticidal activity with the pyrrole insectforest quite, to the bee safely high activity N - oxyl new nicotine analogs insecticide. The insecticide solves the drug resistance of the Imidacloprid and toxic properties of the bees, can be advantageous protection of crops, horticultural plants, fruit and vegetables and the like, to prevent the emergence of the pest, increases its output, while at the same time for the activity and beneficial biological toxicity of the insecticide development explored a new path. (by machine translation)
NOVEL VASCULAR LEAKAGEAGE INHIBITOR
-
Paragraph 0097, (2015/01/07)
The present disclosure relates to a novel vascular leakage inhibitor. The novel vascular leakage inhibitor of the present invention inhibits the apoptosis of vascular endothelial cells, inhibits the formation of actin stress fibers induced by VEGF, and enhances the cortical actin ring structure, thereby inhibiting vascular leakage. Accordingly, the vascular leakage inhibitor of the present invention can prevent or treat various diseases caused by vascular leakage. Since the vascular leakage inhibitor of the present invention is synthesized from commercially available or easily synthesizable pregnenolones, it has remarkably superior feasibility of commercial synthesis.
Synthesis of 1,2-amino alcohols via catalytic C-H amidation of sp3 methyl C-H bonds
Kang, Taek,Kim, Heejeong,Kim, Jeung Gon,Chang, Sukbok
supporting information, p. 12073 - 12075 (2014/12/11)
Herein a new synthetic route to 1,2-amino alcohols is presented by using C-H amidation of sp3 methyl C-H bonds as a key step. Readily available alcohols were employed as starting materials after converting them to removable ketoxime chelating g
Catalytic functionalization of unactivated sp3 C-H bonds via exo -directing groups: Synthesis of chemically differentiated 1,2-Diols
Ren, Zhi,Mo, Fanyang,Dong, Guangbin
supporting information, p. 16991 - 16994,4 (2020/09/02)
We describe a Pd-catalyzed site-selective functionalization of unactivated aliphatic C-H bonds, providing chemically differentiated 1,2-diols from monoalcohol derivatives. The oxime was employed as both a directing group (DG) and an alcohol surrogate for this transformation. As demonstrated in a range of substrates, the C-H bonds β to the oxime group are selectively oxidized. Besides activation of the methyl groups, methylene groups (CH2) in cyclic substrates and methine groups (CH) at bridge-head positions can also be functionalized. In addition, an intriguing oxidative skeleton rearrangement was observed using the menthol-derived substrate. The use of exo-directing groups in C-H activation, as illustrated in this work, would potentially open doors for the discovery of new transformations and new cleavable DGs.
