19486-71-6Relevant academic research and scientific papers
Electrocatalytic Activation of Donor–Acceptor Cyclopropanes and Cyclobutanes: An Alternative C(sp3)?C(sp3) Cleavage Mode
Brandt, Felix,Jacob, Christoph R.,Jones, Peter G.,Kolb, Simon,Petzold, Martin,Werz, Daniel B.
, p. 15928 - 15934 (2021)
We describe the first electrochemical activation of D–A cyclopropanes and D–A cyclobutanes leading after C(sp3)?C(sp3) cleavage to the formation of highly reactive radical cations. This concept is utilized to formally insert molecula
Br?nsted Base-Catalyzed Tandem [2+4] Annulation/Tautomerization/Aromatization Reaction of α-Alkylidene Succinimides with 5-Alkenyl Thiazolones
Ge, Yanqing,Gong, Qi,Gu, Jing,Guo, Hongchao,Luo, Shan,Xie, Lei,Yang, Huimin,Yuan, Chunhao
, p. 3336 - 3347 (2021)
A Br?nsted base-catalyzed tandem [2+4] annulation/tautomerization/aromatization reaction of α-alkylidene succinimides with 5-alkenyl thiazolones has been developed for synthesis of functionalized thiazolo pyrones under mild conditions. The prepared thiazo
SYNTHESIS OF DEUTERATED ALDEHYDES
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Paragraph 0008; 0080, (2021/03/13)
Described are methods for preparing a deuterated aldehyde using N-heterocyclic carbene catalysts in a solvent comprising D2O. The methods may be used to convert a wide variety of aldehydes (e.g., aryl, alkyl, or alkenyl aldehydes) to C-1 deuterated aldehydes under mild reaction conditions without functionality manipulation.
VISIBLE-LIGHT MEDIATED ORGANOPHOTOREDOX CATALYTIC DEUTERATION OF AROMATIC AND ALIPHATIC ALDEHYDES
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Paragraph 0052; 0056; 00103; 00111-00112, (2021/06/22)
Described are methods for preparing a deuterated aldehyde using with a photocatalyst and a hydrogen atom transfer agent in a H2O free solvent comprising D2O and an organic solvent under an inert gas. The methods may be used to convert a wide variety of aldehydes (e.g., aryl, alkyl, or alkenyl aldehydes) to C-1 deuterated aldehydes under mild reaction conditions.
Selective oxidation of alcohol-d1to aldehyde-d1using MnO2
Kitsuwa, Kohei,Kumadaki, Katsushi,Nakayama, Atsushi,Okamura, Hironori,Ozawa, Keita,Shinada, Tetsuro,Tamura, Yusaku,Yamamoto, Yuki,Yasuno, Yoko
, p. 28530 - 28534 (2021/09/22)
The selective oxidation of alcohol-d1to prepare aldehyde-d1was newly developed by means of NaBD4reduction/activated MnO2oxidation. Various aldehyde-d1derivatives including aromatic and unsaturated ald
Zwitterion-induced organic-metal hybrid catalysis in aerobic oxidation
Hu, Rong-Bin,Lam, Ying-Pong,Ng, Wing-Hin,Wong, Chun-Yuen,Yeung, Ying-Yeung
, p. 3498 - 3506 (2021/04/07)
In many metal catalyses, the traditional strategy of removing chloride ions is to add silver salts via anion exchange to obtain highly active catalysts. Herein, we reported an alternative strategy of removing chloride anions from ruthenium trichloride using an organic [P+-N-] zwitterionic compound via multiple hydrogen bond interactions. The resultant organic-metal hybrid catalytic system has successfully been applied to the aerobic oxidation of alcohols, tetrahydroquinolines, and indolines under mild conditions. The performance of zwitterion is far superior to that of many other common Lewis bases or Br?nsted bases. Mechanistic studies revealed that the zwitterion triggers the dissociation of chloride from ruthenium trichloride via nonclassical hydrogen bond interaction. Preliminary studies show that the zwitterion is applicable to catalytic transfer semi-hydrogenation.
Silver-Catalysed Hydroarylation of Highly Substituted Styrenes
Dalton, Toryn,Gre?ies, Steffen,Das, Mowpriya,Niehues, Maximilian,Schrader, Malte L.,Gutheil, Christian,Ravoo, Bart Jan,Glorius, Frank
supporting information, p. 8537 - 8541 (2021/03/16)
Hydroarylation is an effective strategy to rapidly increase the complexity of organic structures by transforming flat alkene moieties into three-dimensional frameworks. Many strategies have already been developed to achieve the hydroarylation of styrenes,
Systematic Evaluation of 1,2-Migratory Aptitude in Alkylidene Carbenes
Dale, Harvey J. A.,Nottingham, Chris,Poree, Carl,Lloyd-Jones, Guy C.
supporting information, p. 2097 - 2107 (2021/02/01)
Alkylidene carbenes undergo rapid inter- and intramolecular reactions and rearrangements, including 1,2-migrations of β-substituents to generate alkynes. Their propensity for substituent migration exerts profound influence over the broader utility of alkylidene carbene intermediates, yet prior efforts to categorize 1,2-migratory aptitude in these elusive species have been hampered by disparate modes of carbene generation, ultrashort carbene lifetimes, mechanistic ambiguities, and the need to individually prepare a series of 13C-labeled precursors. Herein we report on the rearrangement of 13C-alkylidene carbenes generated in situ by the homologation of carbonyl compounds with [13C]-Li-TMS-diazomethane, an approach that obviates the need for isotopically labeled substrates and has expedited a systematic investigation (13C{1H} NMR, DLPNO-CCSD(T)) of migratory aptitudes in an unprecedented range of more than 30 alkylidene carbenes. Hammett analyses of the reactions of 26 differentially substituted benzophenones reveal several counterintuitive features of 1,2-migration in alkylidene carbenes that may prove of utility in the study and synthetic application of unsaturated carbenes more generally.
Differences in the Mechanisms of MnO2Oxidation between Lignin Model Compounds with the p-Hydroxyphenyl, Guaiacyl, and Syringyl Nuclei
Sun, Shirong,Akiyama, Takuya,Yokoyama, Tomoya,Matsumoto, Yuji
, p. 6819 - 6825 (2020/07/02)
The purpose of this study was to examine how the rate and mechanism of MnO2 oxidation differ between the p-hydroxyphenyl (H), guaiacyl (G), and syringyl (S) types of simple nonphenolic lignin model compounds as well as the p-ethylphenyl (E) type compounds. The oxidation was conducted using an excess amount of MnO2 in a sulfate buffer solution at a pH value of 1.5 at room temperature. MnO2 oxidized at least the G and S nuclei, although it commonly oxidizes alcohols present at the benzyl position. The oxidation rates of the benzyl alcohol derivatives were in the order of G- > S- ? H- > E-type, which suggests that the rates are determined by the electronic effects of their methoxy and ethyl functional groups on not only their benzyl positions but also their aromatic π-electron systems. The kinetic isotope effect was observed in the MnO2 oxidations of the same derivatives deuterated at their benzyl hydroxymethyl groups. The observed magnitudes were in the order of E- ? H- > G- ? S-type, suggesting that the contribution of oxidation of their aromatic nuclei, which is another reaction mode of the oxidation of their benzyl positions, increases in the reverse order.
Visible light driven deuteration of formyl C-H and hydridic C(sp3)-H bonds in feedstock chemicals and pharmaceutical molecules
Cao, Hui,Chen, Wei,Chew, Junhong,Kuang, Yulong,Shi, Xiangcheng,Tang, Haidi,Wu, Jie
, p. 8912 - 8918 (2020/09/09)
Deuterium labelled compounds are of significant importance in chemical mechanism investigations, mass spectrometric studies, diagnoses of drug metabolisms, and pharmaceutical discovery. Herein, we report an efficient hydrogen deuterium exchange reaction u
