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Acyl transfer catalysis with 1,2,4-triazole anion.

ABSTRACT: 1,2,4-Triazole anion has been identified as an active acyl transfer catalyst suitable for the aminolysis and transesterification of esters.

SUBMITTER: Yang X

PROVIDER: S-EPMC2696208 | biostudies-literature | 2009 Apr

REPOSITORIES: biostudies-literature

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Acyl transfer catalysis with 1,2,4-triazole anion.

Yang Xing X Birman Vladimir B VB

Organic letters 20090401 7

1,2,4-Triazole anion has been identified as an active acyl transfer catalyst suitable for the aminolysis and transesterification of esters. ...[more]

PMID: 19281231

Similar Datasets

[Hydrogen bis-(1,2,4-triazole)] 1,2,4-triazolium bis-(3-carb-oxy-4-hy-droxy-benzene-sulfonate) 1,2,4-triazole disolvate.

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3-Nitro-1H-1,2,4-triazole.

Project description:The asymmetric unit of the title compound, C(2)H(2)N(4)O(2), contains two crystallographically independent mol-ecules in which the triazole rings are essentially planar, with maximum deviations of 0.003?(1)?Å in both molecules. The dihedral angle between the two 1H-1,2,4-triazole rings is 56.58?(5)°. In the crystal, mol-ecules are linked via inter-molecular N-H?N and C-H?O hydrogen bonds, forming a supra-molecular chain along the b axis.

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1H-1,2,4-Triazole-3-carboxamide.

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Enantioselective 1,1-arylborylation of alkenes: merging chiral anion phase transfer with Pd catalysis.

Project description:A palladium-catalyzed three-component coupling of α-olefins, aryldiazonium salts, and bis(pinacolato)diboron affords direct access to chiral benzylic boronic esters. This process is rendered highly enantioselective using an unprecedented example of cooperative chiral anion phase transfer and transition-metal catalysis.

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Project description:The asymmetric unit of the title compound, C(4)H(5)N(7), comprises two independent but virtually superimposable mol-ecules. Each mol-ecule is planar with the dihedral angles between the five-membered rings being 2.8?(3) and 2.1?(3)°. The crystal structure is formed by an extensive network of relatively strong N-H?N hydrogen-bond inter-actions. Individual mol-ecules are arranged into supra-molecular zigzag chains running parallel to [001] by way of the strongest N-H?N inter-actions. Adjacent chains are inter-connected by rather long (D?A distances range from ca 3.00 to 3.03?Å) but highly directional (inter-action angles above ca 173°) hydrogen bonds forming a supra-molecular layer in the bc plane.

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Project description:Catalysts that can promote acyl transfer processes are important to enantioselective synthesis and their development has received significant attention in recent years. Despite noteworthy advances, discovery of small-molecule catalysts that are robust, efficient, recyclable and promote reactions with high enantioselectivity can be easily and cost-effectively prepared in significant quantities (that is, >10?g) has remained elusive. Here, we demonstrate that by attaching a binaphthyl moiety, appropriately modified to establish H-bonding interactions within the key intermediates in the catalytic cycle, and a 4-aminopyridyl unit, exceptionally efficient organic molecules can be prepared that facilitate enantioselective acyl transfer reactions. As little as 0.5?mol% of a member of the new catalyst class is sufficient to generate acyl-substituted all-carbon quaternary stereogenic centres in quantitative yield and in up to 98:2 enantiomeric ratio (er) in 5?h. Kinetic resolution or desymmetrization of 1,2-diol can be performed with high efficiency and enantioselectivity as well.

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Project description:Enzymes are encoded with a gamut of information to catalyze a highly selective transformation by selecting the proper reactants from an intricate mixture of constituents. Mimicking biological machinery, two switchable catalysts with differently sized cavities and allosteric control are conceived that allow complementary size-selective acyl transfer in an on/off manner by modulating the effective local concentration of the substrates. Selective activation of one of two catalysts in a mixture of reactants of similar reactivity enabled upregulation of the desired product.

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A combination of directing groups and chiral anion phase-transfer catalysis for enantioselective fluorination of alkenes.

Project description:We report a catalytic enantioselective electrophilic fluorination of alkenes to form tertiary and quaternary C(sp3)-F bonds and generate ?-amino- and ?-aryl-allylic fluorides. The reaction takes advantage of the ability of chiral phosphate anions to serve as solid-liquid phase transfer catalysts and hydrogen bond with directing groups on the substrate. A variety of heterocyclic, carbocyclic, and acyclic alkenes react with good to excellent yields and high enantioselectivities. Further, we demonstrate a one-pot, tandem dihalogenation-cyclization reaction, using the same catalytic system twice in series, with an analogous electrophilic brominating reagent in the second step.

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Poly[(?(3)-hydrogenphosphato)(4H-1,2,4-triazole-?N(1))zinc].

Project description:The asymmetric unit of the title compound, [Zn(HPO(4))(C(2)H(3)N(3))](n), contains one Zn(2+) cation, one (HPO(4))(2-) anion and a 1,2,4 triazole ligand. The Zn(2+) cation is coordinated in a quite regular tetra-hedral geometry by O atoms from three phosphate groups and a tertiary N atom from the triazole ring. Each phosphate anion is connected to three Zn(II) cations, leading to a series of corrugated organic-inorganic layers parallel to the ac plane. The overall structure involves stacking of complex hybrid organic-inorganic layers along the b axis. Cohesion in the crystal is ensured by an infinite three-dimensional network of N-H?O and O-H?O hydrogen bonds between the phosphate groups and the triazole ligands.

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