13391-45-2Relevant academic research and scientific papers
Asymmetric synthesis of diarylmethanols: Development of a hemilabile phosphorus ligand based on the concept of conformational control
Arao, Takafumi,Suzuki, Kiyoto,Kondo, Kazuhiro,Aoyama, Toyohiko
, p. 3809 - 3814 (2006)
The asymmetric synthesis of diarylmethanols using a new hemilabile phosphorus ligand based on the concept of conformational control is described. Georg Thieme Verlag Stuttgart.
Grignard Reagents on a Tab: Direct Magnesium Insertion under Flow Conditions
Huck, Lena,De La Hoz, Antonio,Díaz-Ortiz, Angel,Alcázar, Jesus
, p. 3747 - 3750 (2017)
An on-demand preparation of organomagnesium reagents is presented using a new flow protocol. The risks associated with the activation of magnesium are circumvented by a new on-column initiation procedure. Required amounts of solutions with a precise titration were obtained. Telescoped flow or batch reactions allow access to a diverse set of functional groups.
Structure-Based Design of High-Affinity Fluorescent Probes for the Neuropeptide Y Y1Receptor
Müller, Christoph,Gleixner, Jakob,Tahk, Maris-Johanna,Kopanchuk, Sergei,Laasfeld, T?nis,Weinhart, Michael,Schollmeyer, Dieter,Betschart, Martin U.,Lüdeke, Steffen,Koch, Pierre,Rinken, Ago,Keller, Max
, p. 4832 - 4853 (2022/03/27)
The recent crystallization of the neuropeptide Y Y1 receptor (Y1R) in complex with the argininamide-type Y1R selective antagonist UR-MK299 (2) opened up a new approach toward structure-based design of nonpeptidic Y1R ligands. We designed novel fluorescent probes showing excellent Y1R selectivity and, in contrast to previously described fluorescent Y1R ligands, considerably higher (～100-fold) binding affinity. This was achieved through the attachment of different fluorescent dyes to the diphenylacetyl moiety in 2 via an amine-functionalized linker. The fluorescent ligands exhibited picomolar Y1R binding affinities (pKi values of 9.36-9.95) and proved to be Y1R antagonists, as validated in a Fura-2 calcium assay. The versatile applicability of the probes as tool compounds was demonstrated by flow cytometry- and fluorescence anisotropy-based Y1R binding studies (saturation and competition binding and association and dissociation kinetics) as well as by widefield and total internal reflection fluorescence (TIRF) microscopy of live tumor cells, revealing that fluorescence was mainly localized at the plasma membrane.
Light-driven MPV-type reduction of aryl ketones/aldehydes to alcohols with isopropanol under mild conditions
Cao, Dawei,Xia, Shumei,Pan, Pan,Zeng, Huiying,Li, Chao-Jun,Peng, Yong
supporting information, p. 7539 - 7543 (2021/10/12)
Alcohols are versatile structural motifs of pharmaceuticals, agrochemicals and fine chemicals. With respect to green chemistry, the development of more sustainable and cost-efficient processes for converting ketones/aldehydes to alcohols is highly desired. Herein, a direct light-driven strategy for reducing ketones/aldehydes to alcohols using isopropanol as the reducing agent and solvent, in the presence of t-BuOLi, under an air atmosphere at room temperature is developed. This operationally simple light-promoted Meerwein-Ponndorf-Verley (MPV) type reduction can be used to produce various benzylic alcohol derivatives as well as applied to bioactive molecules and PEEK model compounds, demonstrating its application potential.
CoI-Catalyzed Barbier Reactions of Aromatic Halides with Aromatic Aldehydes and Imines
Presset, Marc,Paul, Jér?me,Cherif, Ghania Nait,Ratnam, Nisanthan,Laloi, Nicolas,Léonel, Eric,Gosmini, Corinne,Le Gall, Erwan
supporting information, p. 4491 - 4495 (2019/02/27)
The reductive Barbier coupling of aromatic halides and electrophiles has been achieved using a CoBr2/1,10-phenanthroline catalytic system and over stoichiometric amounts of zinc. The reaction displayed a broad scope of substrates, including (hetero)aryl chlorides as pro-nucleophiles and aldehydes or imines as electrophiles, leading to diarylmethanols and diarylmethylamines in moderate to excellent yields, respectively.
Synthesis method for diaryl methanol compound
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Paragraph 0074; 0075; 0076; 0077; 0102; 0103-0123, (2018/03/26)
The technical solution and content of the invention relate to a synthesis method for a diaryl methanol compound shown as formula (I); the formula (I) is shown in the specification. The method includesthe following steps: under the existence of a palladium-sourced compound catalyst and organic phosphine ligand, in an organic solvent, an aldehyde derivative shown as formula (II) reacts with an organic cyclic triolborate compound shown as formula (III), and after the reaction is completed, post-processing is carried out, so that the diaryl methanol compound shown as formula (I) is obtained. According to the method, the reaction between the aldehyde compound and the organic cyclic triolborate compound can be smoothly carried out, so that the diaryl methanol compound can be obtained at high yield, a brand new synthesis route is provided for the synthesis of the compound, and a good application prospect and good industrial value are achieved.
Generation of Aryl and Heteroaryl Magnesium Reagents in Toluene by Br/Mg or Cl/Mg Exchange
Ziegler, Dorothée S.,Karaghiosoff, Konstantin,Knochel, Paul
supporting information, p. 6701 - 6704 (2018/05/05)
The alkylmagnesium alkoxide sBuMgOR?LiOR (R=2-ethylhexyl), which was prepared as a 1.5 m solution in toluene, undergoes very fast Br/Mg exchange with aryl and heteroaryl bromides, producing aryl and heteroaryl magnesium alkoxides (ArMgOR?LiOR) in toluene. These Grignard reagents react with a broad range of electrophiles, including aldehydes, ketones, allyl bromides, acyl chlorides, epoxides, and aziridines, in good yields. Remarkably, the related reagent sBu2Mg?2 LiOR (R=2-ethylhexyl) undergoes Cl/Mg exchange with various electron-rich aryl chlorides in toluene, producing diorganomagnesium species of type Ar2Mg?2 LiOR, which react well with aldehydes and allyl bromides.
Coupling of aromatic aldehydes with aryl halides in the presence of nickel catalysts with diazabutadiene ligands
Asachenko,Valaeva,Kudakina,Uborsky,Izmer,Kononovich,Voskoboynikov
, p. 456 - 463 (2017/03/08)
Nickel catalysts with diazabutadiene ligands promote cross-coupling of benzaldehydes with aryl halides in the presence of zinc as reducing agent, which leads to the corresponding benzhydrols and benzophenones. The benzophenone percentage considerably increases when lithium chloride additive is used.
Exploring the Reactivity of α-Lithiated Aryl Benzyl Ethers: Inhibition of the [1,2]-Wittig Rearrangement and the Mechanistic Proposal Revisited
Velasco, Rocío,Silva López, Carlos,Nieto Faza, Olalla,Sanz, Roberto
, p. 15058 - 15068 (2016/10/11)
By carefully controlling the reaction temperature, treatment of aryl benzyl ethers with tBuLi selectively leads to α-lithiation, generating stable organolithiums that can be directly trapped with a variety of selected electrophiles, before they can undergo the expected [1,2]-Wittig rearrangement. This rearrangement has been deeply studied, both experimentally and computationally, with aryl α-lithiated benzyl ethers bearing different substituents at the aryl ring. The obtained results support the competence of a concerted anionic intramolecular addition/elimination sequence and a radical dissociation/recombination sequence for explaining the tendency of migration for aryl groups. The more favored rearrangements are found for substrates with electron-poor aryl groups that favor the anionic pathway.
Electronic effects on the substitution reactions of benzhydrols and fluorenyl alcohols. Determination of mechanism and effects of antiaromaticity
George, Stephen R. D.,Elton, Timothy E.,Harper, Jason B.
supporting information, p. 10745 - 10750 (2015/11/17)
A range of substituted benzhydrols and fluorenols were prepared and subjected to acid catalysed methanolysis. Analysis of the rates of each of these processes showed correlation with Hammett σ+ parameters as is consistent with the significant build-up of positive charge adjacent to the ring. In combination with the similarity of the electronic susceptibility of the processes, these data suggest that both reactions proceed through a unimolecular rate-determining step. This shows that the effect of fusion of the phenyl systems (and hence potentially introducing an antiaromatic carbocation intermediate) is only to slow the rate of reaction rather than change the mechanism of the process.
