71813-50-8Relevant academic research and scientific papers
Access to Trisubstituted Fluoroalkenes by Ruthenium-Catalyzed Cross-Metathesis
Nouaille, Augustin,Pannecoucke, Xavier,Poisson, Thomas,Couve-Bonnaire, Samuel
, p. 2140 - 2147 (2021/03/06)
Although the olefin metathesis reaction is a well-known and powerful strategy to get alkenes, this reaction remained highly challenging with fluororalkenes, especially the Cross-Metathesis (CM) process. Our thought was to find an easy accessible, convenient, reactive and post-functionalizable source of fluoroalkene, that we found as the methyl 2-fluoroacrylate. We reported herein the efficient ruthenium-catalyzed CM reaction of various terminal and internal alkenes with methyl 2-fluoroacrylate giving access, for the first time, to trisubstituted fluoroalkenes stereoselectively. Unprecedent TON for CM involving fluoroalkene, up to 175, have been obtained and the reaction proved to be tolerant and effective with a large range of olefin partners giving fair to high yields in metathesis products. (Figure presented.).
Hydrophosphination using [GeCl{N(SiMe3)2}3] as a pre-catalyst
Barrett,Sanderson,Mahon,Webster
supporting information, p. 13623 - 13626 (2020/11/17)
Transformations catalyzed by germanium are scarce, with examples mainly limited to widely catalyzed processes such as polymerisation of lactide and hydroboration of carbonyls. Reported is the first example of hydrophosphination using a germanium pre-catalyst, yielding anti-Markovnikov products when diphenylphosphine is reacted with styrenes or internal alkynes at room temperature. This journal is
Stereoselective Convergent Synthesis of Tetrahydro-5 H-benzo[c]fluorene via Nine-Membered Ring-Closing Metathesis and Transannular Acid-Mediated Cyclization/Nucleophilic Addition
Lekky, Anek,Ruengsatra, Tanachote,Ruchirawat, Somsak,Ploypradith, Poonsakdi
, p. 5277 - 5291 (2019/05/10)
The diene methyl ethers or acetates, constructed from the Li-Br exchange/addition reactions of 2-vinylbenzaldehydes and 2-(but-3-en-1-yl)bromoarenes followed by etherification or acetylation of the corresponding alcohols, smoothly underwent the ring-closi
Umpolung of Carbonyl Groups as Alkyl Organometallic Reagent Surrogates for Palladium-Catalyzed Allylic Alkylation
Zhu, Dianhu,Lv, Leiyang,Li, Chen-Chen,Ung, Sosthene,Gao, Jian,Li, Chao-Jun
supporting information, p. 16520 - 16524 (2018/11/23)
Palladium-catalyzed allylic alkylation of nonstabilized carbon nucleophiles is difficult and remains a major challenge. Reported here is a highly chemo- and regioselective direct palladium-catalyzed C-allylation of hydrazones, generated from carbonyls, as a source of umpolung unstabilized alkyl carbanions and surrogates of alkyl organometallic reagents. Contrary to classical allylation techniques, this umpolung reaction utilizes hydrazones prepared not only from aryl aldehydes but also from alkyl aldehydes and ketones as renewable feedstocks. This strategy complements the palladium-catalyzed coupling of unstabilized nucleophiles with allylic electrophiles by providing an efficient and selective catalytic alternative to the traditional use of highly reactive alkyl organometallic reagents.
Direct allylation of benzyl alcohols, diarylmethanols, and triarylmethanols mediated by XtalFluor-E
Lebleu, Thomas,Paquin, Jean-Fran?ois
supporting information, p. 442 - 444 (2017/01/10)
We report the direct allylation of benzyl alcohols, diarylmethanols and triarylmethanols mediated by XtalFluor-E using allyltrimethylsilane. The resulting allylated products are obtained in moderate to high yield.
Application of Dehydroabietic Acid in Palladium-Catalysed Enyne Cycloisomerisation
Wu, Na,Li, Ruikun,Cui, Feihu,Pan, Yingming
supporting information, p. 2442 - 2447 (2017/07/22)
Dehydroabietic acid (DAA) promotes palladium(0)-catalysed cyclisations of arene-tethered 1,7-enynols and 1,m-enynoates (m=6,7) to give fused carbocyclic dienes. 6,6,6,5-Tetracyclic lactones are accessible by one-pot cycloisomerisation/Diels–Alder reaction
1,3,8-TRIAZASPIRO[4,5]DECAN-4-ONE DERIVATIVES USEFUL FOR THE TREATMENT OF ORL-1 RECEPTOR MEDIATED DISORDERS
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Paragraph 0238-0240, (2017/02/28)
The present invention is directed to novel 1,3,8-triazaspiro[4.5]decan-4-one derivatives of the general formulawherein all variables are as defined herein, useful in the treatment of disorders and conditions mediated by the ORL-1 G-protein coupled receptor. More particularly, the compounds of the present invention are useful in the treatment of disorders and conditions such as anxiety, depression, substance abuse, neuropathic pain, acute pain, migraine, asthma, cough and for improved cognition.
Aryl radical cyclization with alkyne followed by tandem carboxylation in methyl 4-tert-butylbenzoate-mediated electrochemical reduction of 2-(2-propynyloxy)bromobenzenes in?the presence of carbon dioxide
Katayama, Asahi,Senboku, Hisanori,Hara, Shoji
, p. 4626 - 4636 (2016/07/18)
Constant current electrolysis of 2-(2-propynyloxy)bromobenzenes in DMF using an undivided cell equipped with a Pt cathode and an Mg anode in the presence of carbon dioxide and an electron transfer mediator, methyl 4-tert-butylbenzoate, resulted in aryl ra
Characterization of the Dynamic Equilibrium between Closed and Open Forms of the Benzoxaborole Pharmacophore
Vshyvenko, Sergey,Clapson, Marissa L.,Suzuki, Itaru,Hall, Dennis G.
, p. 1097 - 1101 (2016/12/18)
Benzoxaboroles are a class of five-membered hemiboronic acids that recently attracted significant attention as a new pharmacophore on account of their unique structural and physicochemical properties and their ability to interact selectively with biomolecules. Their structural behavior in water and its effect on their physiological properties remain unclear, especially the question of dynamic hydrolytic equilibrium of the oxaborole ring. Herein, we used NMR spectroscopy, in mixed aqueous-organic solvent, to confirm the strong preference for the closed form of benzoxaborole and its six- and seven-membered homologues over the open boronic acid form. Only with the eight-membered homologue does the cyclic form become unfavorable. Using dynamic VT-NMR studies with designed probe compound 20, we demonstrate that the oxaborole ring undergoes rapid hydrolytic ring closing-opening at ambient temperature at a rate of >100 Hz via a mechanism featuring rate-limiting proton-transfer steps. This knowledge can help provide a better understanding of the behavior of benzoxaboroles in biological systems.
Iridium-catalyzed borylation of secondary benzylic C-H bonds directed by a hydrosilane
Cho, Seung Hwan,Hartwig, John F.
supporting information, p. 8157 - 8160 (2013/07/05)
Most functionalizations of C-H bonds by main-group reagents occur at aryl or methyl groups. We describe a highly regioselective borylation of secondary benzylic C-H bonds catalyzed by an iridium precursor and 3,4,7,8-tetramethyl-1, 10-phenanthroline as the ligand. The reaction is directed to the benzylic position by a hydrosilyl substituent. This hydrosilyl directing group is readily deprotected or transformed to other functional groups after the borylation reaction, providing access to a diverse set of secondary benzylboronate esters by C-H borylation chemistry.
