781-35-1Relevant academic research and scientific papers
Benzyl C–O and C–N Bond Construction via C–C Bond Dissociation of Oxime Ester under Visible Light Irradiation
Fan, Xiuwei,Lei, Tao,Liu, Zan,Yang, Xiu-Long,Cheng, Yuan-Yuan,Liang, Ge,Chen, Bin,Tung, Chen-Ho,Wu, Li-Zhu
, p. 1551 - 1558 (2019/09/09)
A photoredox benzyl activation was developed via formidable C(sp3)–C(sp3) bond dissociation of 1-aryl acetone oxime esters, which were easily prepared from benzyl ketones. Further coupling with O- and N- nucleophiles successfully forged important benzyl ether and amines derivatives in one pot. In this process, different substitutions on oxime esters were found compatible and various primary and secondary alcohols and amines, as well as amides showed good performance as nucleophiles. Mechanistic studies by control experiments, electrochemical measurements and in-situ NMR spectra proposed a N–O bond interruption/C–C bond fragmentation/oxidation sequence to provide the key cation intermediate for the next electrophilic SN process. The features of mild condition, short reaction time and broad substrate scope made this new strategy much promising in the transformation of benzyl compounds, which might be valuable in last-stage functionalizations.
SYNTHESIS OF HYPERVALENT IODINE REAGENTS WITH DIOXYGEN
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Paragraph 0114-0117; 0138-0139, (2019/01/15)
Methods of synthesis of hypervalent iodine reagents and methods for oxidation of organic compounds are disclosed.
Catalytic Alkyne Arylation Using Traceless Directing Groups
Park, Jung-Woo,Kang, Bubwoong,Dong, Vy M.
, p. 13598 - 13602 (2018/09/25)
By using Pd0/Mandyphos, we achieved a three-component aminoarylation of alkynes to generate enamines, which are then hydrolyzed to either α-arylphenones or α,α-diarylketones. This Pd-catalyzed method overcomes established known pathways to enable the use of amines as traceless directing groups for C?C bond formation.
Oxidation Catalysis by an Aerobically Generated Dess–Martin Periodinane Analogue
Maity, Asim,Hyun, Sung-Min,Wortman, Alan K.,Powers, David C.
supporting information, p. 7205 - 7209 (2018/05/29)
Hypervalent iodine(V) reagents, such as Dess–Martin periodinane (DMP) and 2-iodoxybenzoic acid (IBX), are broadly useful oxidants in chemical synthesis. Development of strategies to generate these reagents from dioxygen (O2) would immediately enable use of O2 as a terminal oxidant in a broad array of substrate oxidation reactions. Recently we disclosed the aerobic synthesis of I(III) reagents by intercepting reactive oxidants generated during aldehyde autoxidation. In this work, aerobic oxidation of iodobenzenes is coupled with disproportionation of the initially generated I(III) compounds to generate I(V) reagents. The aerobically generated I(V) reagents exhibit substrate oxidation chemistry analogous to that of DMP. The developed aerobic generation of I(V) has enabled the first application of I(V) intermediates in aerobic oxidation catalysis.
Rhenium complex-catalyzed Meinwald rearrangement reactions of oxiranes
Umeda, Rui,Muraki, Masahito,Nakamura, Yuudai,Tanaka, Tomoyuki,Kamiguchi, Kyohei,Nishiyama, Yutaka
, p. 2393 - 2395 (2017/05/29)
The Meinwald rearrangement reaction of oxiranes to the corresponding carbonyl compounds is efficiently catalyzed by the ReBr(CO)5 complex.
Synthesis of 1,3-Cycloalkadienes from Cycloalkenes: Unprecedented Reactivity of Oxoammonium Salts
Nagasawa, Shota,Sasano, Yusuke,Iwabuchi, Yoshiharu
supporting information, p. 13189 - 13194 (2016/10/30)
Few methods allow for the direct conversion of cycloalkenes into cycloalkadienes with high chemo- and regioselectivity. Herein, we report a convenient one-pot process for this transformation that involves the unprecedented N-preferential group transfer of N-oxoammonium salts to cycloalkenes, followed by Cope elimination, to afford cycloalkadienes at room temperature and pressure.
PROCESS FOR CREATING CARBON-CARBON BONDS USING CARBONYL COMPOUNDS
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Paragraph 0426-0427, (2015/06/24)
The present invention concerns a process for preparing a compound of formula (I) by reaction between a compound of formula (II) and a compound of formula (III) in the presence of a copper-containing catalyst, a ligand and base. The invention also concerns the implementing of this process for the preparation of building blocks to prepare molecules of interest in particular in the pharmaceutical, agro-chemical fields, etc.
4-CH3CONH-TEMPO/Peracetic Acid System for a Shortened Electron-Transfer-Cycle-Controlled Oxidation of Secondary Alcohols
Zhang, Shufang,Miao, Chengxia,Xia, Chungu,Sun, Wei
, p. 1865 - 1870 (2015/06/23)
We have developed a 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) derivative catalyzed oxidation of secondary alcohols with peracetic acid as the oxidant, which was generated from H2O2 and acetic acid catalyzed by strongly acidic resins. The oxidation of alcohols proceeded well through a shortened electron-transfer cycle under metal-free conditions, avoiding the use of any other electron-transfer mediators such as halides. In addition, we demonstrated that the present system exhibited excellent efficiency under mild conditions for the oxidation of aromatic, aliphatic, and allylic secondary alcohols. Shortcut to ketones: The 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO)-derivative-catalyzed oxidation of secondary alcohols employing peracetic acid generated from H2O2 and acetic acid with strongly acidic resins proceeds through a shortened electron-transfer cycle without halide additives. The system not only exhibits excellent efficiency at room temperature but also has a wide substrate scope.
AZA-PYRIDONE COMPOUNDS AND USES THEREOF
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Paragraph 0165; 0166, (2015/03/16)
Disclosed herein are aza-pyridone compounds, pharmaceutical compositions that include one or more aza-pyridone compounds, and methods of synthesizing the same. Also disclosed herein are methods of ameliorating and/or treating a disease and/or a condition, including an orthomyxovirus infection, with an aza-pyridone compounds. Examples of an orthomyxovirus viral infection include an influenza infection.
Oxidative kinetic resolution of racemic secondary alcohols in water with chiral PNNP/Ir catalyst
Zhang, Juanni,Yang, Xiangren,Zhou, Han,Li, Yanyun,Dong, Zhenrong,Gao, Jingxing
supporting information; experimental part, p. 1289 - 1292 (2012/06/18)
Using water as solvent, the oxidative kinetic resolution of a wide range of racemic secondary alcohols with a chiral PNNP/Ir catalyst was investigated. The catalytic reaction proceeded smoothly with excellent enantioselectivity (up to 97% ee) under mild conditions, providing an environmentally benign process to achieve optically active alcohols.
