95119-41-8Relevant academic research and scientific papers
Synthesis Method of Cyclopropane or Cyclopentene Derivatives via Fe-catalyzed Cationic Radical Cycloaddition Reaction
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Paragraph 0080-0081; 0101-0102, (2021/11/02)
In this disclosure Fe (III) complex is used as an electron oxidizing agent to oxidize an electron - rich alkene compound to form a radical cation intermediate, and then a cyclopropane compound or 3 5-membered ring compound is synthesized by inducing a cycloaddition reaction with the diazo compound.
Cycloaddition Reactions of Alkene Radical Cations using Iron(III)-Phenanthroline Complex
Cho, Yong Hyun,Kim, Jae Hyung,An, Hyeju,Ahn, Kwang-Hyun,Kang, Eun Joo
supporting information, p. 2183 - 2188 (2020/04/29)
Single electron oxidation of electron-rich alkenes using the iron(III)-phenanthroline complex produced electrophilic alkene radical cations, which promoted efficient radical cation [2+1] cycloaddition reactions with diazo compounds. Subsequent chain propagation afforded tri- and tetra-substituted cyclopropanes. This methodology was also expanded to [3+2] cycloaddition reactions with vinyl diazoesters, validating this sustainable, first-row transition metal iron system for the single electron redox reactions. (Figure presented.).
Cyclopropane-alkene metathesis by gold(i)-catalyzed decarbenation of persistent cyclopropanes
Mato, Mauro,Martín-Torres, Inmaculada,Herlé, Bart,Echavarren, Antonio M.
supporting information, p. 4216 - 4219 (2019/05/06)
A gold(i)-catalyzed cyclopropane-alkene metathesis has been demonstrated with two new families of cyclopropane derivatives of naphthalene and phenanthrene (benzo-fused norcaradienes). In this process, metal carbene units are transferred from a persistent
Rhodium Porphyrin Catalyzed Regioselective Transfer Hydrogenolysis of C-C σ-Bonds in Cyclopropanes with iPrOH
Chen, Chen,Feng, Shiyu,Chan, Kin Shing
supporting information, p. 2582 - 2589 (2019/07/02)
A new rhodium porphyrin catalyzed regioselective transfer hydrogenolysis of both activated and unactivated cyclopropanes employing iPrOH as the hydrogen source was discovered. The reaction mechanism for the C-C σ-bond activation of cyclopropanes was identified through an initial radical substitution with rhodium(II) metalloporphyrin radical to give a rhodium porphyrin alkyl, followed by hydrogenolysis with iPrOH to give the corresponding acyclic alkanes and regenerate rhodium(II) metalloporphyrin radical.
A transition-metal-free & diazo-free styrene cyclopropanation
Herraiz, Ana G.,Suero, Marcos G.
, p. 9374 - 9379 (2019/10/22)
An operationally simple and broadly applicable novel cyclopropanation of styrenes using gem-diiodomethyl carbonyl reagents has been developed. Visible-light triggered the photoinduced generation of iodomethyl carbonyl radicals, able to cyclopropanate a wide array of styrenes with excellent chemoselectivity and functional group tolerance. To highlight the utility of our photocyclopropanation, we demonstrated the late-stage functionalization of biomolecule derivatives.
Radical Cation Cyclopropanations via Chromium Photooxidative Catalysis
Sarabia, Francisco J.,Ferreira, Eric M.
supporting information, p. 2865 - 2868 (2017/06/07)
The chromium photocatalyzed cyclopropanation of diazo reagents with electron-rich alkenes is described. The transformation occurs under mild conditions and features specific distinctions from traditional diazo-based cyclopropanations (e.g., avoiding β-hydride elimination, chemoselectivity considerations, etc.). The reaction appears to work most effectively using chromium catalysis, and a number of decorated cyclopropanes can be accessed in generally good yields.
Spin-selective generation of triplet nitrenes: Olefin aziridination through visible-light photosensitization of azidoformates
Scholz, Spencer O.,Farney, Elliot P.,Kim, Sangyun,Bates, Desiree M.,Yoon, Tehshik P.
supporting information, p. 2239 - 2242 (2016/02/18)
Azidoformates are interesting potential nitrene precursors, but their direct photochemical activation can result in competitive formation of aziridination and allylic amination products. Herein, we show that visible-light-activated transition-metal comple
Wittig reagents as metallocarbene precursors: In situ generated monocarbonyl iodonium ylides
Ho, Phyllis E.,Tao, Jason,Murphy, Graham K.
supporting information, p. 6540 - 6544 (2013/11/06)
A proof of concept study was undertaken to determine the suitability of monocarbonyl iodonium ylides (MCIYs) as metallocarbene precursors. Exposing Wittig reagents to iodosylbenzene results in a pseudo-Wittig reaction that generates MCIYs in situ. These ylides are intercepted by transition-metal catalysts to generate metallocarbenes, which then undergo either dimerization or cyclopropanation reactions with a variety of alkenes. Additionally, the reaction between diazoester-derived metallocarbenes and Wittig reagents afforded cross-coupling products, illustrating a new type of olefination reaction for phosphonium ylides. Monocarbonyl iodonium ylides (MCIYs) represent a possible alternative to the use diazoketones and -esters as metallocarbene precursors. Upon treatment with iodosylbenzene, a Wittig reagent will undergo ylide transfer to generate a MCIY in situ. In the presence of transition-metal catalysts, MCIYs serve as precursors to metallocarbenes, which undergo dimerization or cyclopropanation of alkenes. tfacac = trifluoroacetylacetonate. Copyright
The influence of chiral auxiliaries is enhanced within zeolites
Jayaraman,Uppili,Natarajan,Joy,Chong,Netherton,Zenova,Scheffer,Ramamurthy
, p. 8231 - 8235 (2007/10/03)
Zeolites significantly enhance the influence of chiral auxiliaries during photochemical reactions. The generality of this phenomenon has been tested with three independent examples. Chiral auxiliaries that lead to 1:1 mixtures of diastereomers in solution
Acyl guanidine sodium/proton exchange inhibitors and method
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, (2008/06/13)
Acyl guanidines are provided which are sodium/proton exchange (NHE) inhibitors which have the structure STR1 wherein n is 1 to 5; X is N or C--R5 wherein R5 is H, halo, alkenyl, alkynyl, alkoxy, alkyl, aryl or heteroaryl; and R1, R2, R3 and R4 are as defined herein, and where X is N, R1 is preferably aryl or heteroaryl, and are useful as antianginal and cardioprotective agents. In addition, a method is provided for preventing or treating angina pectoris, cardiac dysfunction, myocardial necrosis, and arrhythmia employing the above acyl guanidines.
