- Direct hydroxyethylation of amines by carbohydrates: Via ruthenium catalysis
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An efficient and halogen-free catalytic methodology for the synthesis of β-amino alcohols from aromatic amines and biomass-derived carbohydrates is demonstrated for the first time. The activation of C5/C6 sugars by a ruthenium catalyst selectively generates the C2 alkylating reagent glycolaldehyde. The transformation involves metal-catalyzed hydrogen borrowing for the reduction of the imine intermediate. A series of arylamines bearing various substituents were successfully transformed into the desired products in good to excellent yields.
- Jia, Le,Makha, Mohamed,Du, Chen-Xia,Quan, Zheng-Jun,Wang, Xi-Cun,Li, Yuehui
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p. 3127 - 3132
(2019/06/18)
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- Tetragonal versus hexagonal: Structure-dependent catalytic activity of Co/Zn bimetallic metal-organic frameworks
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Tetragonal and hexagonal phases of monometallic Zn and bimetallic Co/Zn metal-organic frameworks (MOFs), with secondary building units (SBUs) containing a M3O (M = metal) cluster, were synthesized from identical constituents using a benzenetricarboxylate (BTC3-) linker that forms decorated 3,6- and 3,5-connected networks, respectively. There exist subtle differences between the SBUs; one of the metal atoms in the M3O cluster in the tetragonal phase has one dissociable DMF solvent molecule while that in the hexagonal phase has three. Connectivities between the SBUs form one-dimensional channels in both MOFs. These MOFs catalyze the chemoselective addition of amines to epoxides, giving exclusively β-hydroxyamine under heterogeneous conditions. A ring-opening reaction of a symmetrical epoxide showed that the hexagonal phase diastereoselectively yields trans-alcohol, exhibiting an exquisite model for structure-dependent activity.
- Pariyar, Anand,Asl, Hooman Yaghoobnejad,Choudhury, Amitava
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supporting information
p. 9250 - 9257
(2016/09/28)
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- Mild and phosphine-free iron-catalyzed cross-coupling of nonactivated secondary alkyl halides with alkynyl grignard reagents
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A simple protocol for iron-catalyzed cross-coupling of nonactivated secondary alkyl bromides and iodides with alkynyl Grignard reagents at room temperature has been developed. A wide range of secondary alkyl halides and terminal alkynes are tolerated to a
- Cheung, Chi Wai,Ren, Peng,Hu, Xile
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p. 2566 - 2569
(2014/05/20)
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- Bioconjugatable azo-based dark-quencher dyes: Synthesis and application to protease-activatable far-red fluorescent probes
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We describe the efficient synthesis and one-step derivatization of novel, nonfluorescent azo dyes based on the Black Hole Quencher-3 (BHQ-3) scaffold. These dyes were equipped with various reactive and/or bioconjugatable groups (azido, α-iodoacetyl, keton
- Chevalier, Arnaud,Massif, Cédrik,Renard, Pierre-Yves,Romieu, Anthony
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p. 1686 - 1699
(2013/04/10)
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- Process for preparing optically active secondary alcohols having nitrogenous or oxygenic functional groups
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A process for preparing optically active secondary alcohols of the general formula (3), [wherein R1 is linear lower alkyl, an aromatic ring group, or the like; A is CH2NR2R3 or the like; n is an integer of 0 to 2; and * represents an asymmetric carbon atom] by asymmetrically hydrogenating a ketone compound of the general formula (1) having nitrogenous or oxygen functional group at any of the a-, β- and γ-positions, with selectivity among functional groups by the use of a ruthenium/optically active bidentate phosphine/diamine complex as the catalyst in the presence of hydrogen alone or together with a base. The optically active secondary alcohols obtained by the process are useful as drugs and intermediates for the preparation of drugs.
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