Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

New Stable Cu(I) Catalyst Supported on Weakly Acidic Polyacrylate Resin for Green C-N Coupling: Synthesis of N-(Pyridin-4-yl)benzene Amines and N,N-Bis(pyridine-4-yl)benzene Amines.

ABSTRACT: A method for preparation of a new stable Cu(I) catalyst supported on weakly acidic polyacrylate resin without additional stabilizing ligands is described. A simple and efficient methodology for Ullmann Cu(I) catalyzed C-N cross coupling reactions using this original catalyst is reported. Coupling reactions of 4-chloropyridinium chloride with anilines containing electron donating (EDG) or electron withdrawing (EWG) groups, naphthalen-2-amine and piperazine, respectively, are successfully demonstrated.

SUBMITTER: Kore N

PROVIDER: S-EPMC6155682 | biostudies-literature | 2016 Dec

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

New Stable Cu(I) Catalyst Supported on Weakly Acidic Polyacrylate Resin for Green C-N Coupling: Synthesis of N-(Pyridin-4-yl)benzene Amines and N,N-Bis(pyridine-4-yl)benzene Amines.

Kore Nitin N Pazdera Pavel P

Molecules (Basel, Switzerland) 20161222 1

A method for preparation of a new stable Cu(I) catalyst supported on weakly acidic polyacrylate resin without additional stabilizing ligands is described. A simple and efficient methodology for Ullmann Cu(I) catalyzed C-N cross coupling reactions using this original catalyst is reported. Coupling reactions of 4-chloropyridinium chloride with anilines containing electron donating (EDG) or electron withdrawing (EWG) groups, naphthalen-2-amine and piperazine, respectively, are successfully demonstr ...[more]

PMID: 28025513

Similar Datasets

1,2,4,5-Tetra-fluoro-3,6-diiodo-benzene-4-(pyridin-4-ylsulfan-yl)pyridine (1/1).

Project description:The asymmetric unit of the title 1:1 adduct, C(10)H(8)N(2)S·C(6)F(4)I(2), comprises a half-mol-ecule of 1,2,4,5-tetra-fluoro-3,6-diiodo-benzene, and half a 4-(pyridin-4-ylsulfan-yl)pyridine mol-ecule. The former is completed by crystallographic inversion symmetry, the latter by twofold symmetry, with the S atom lying on the rotation axis. The almost planar 1,2,4,5-tetra-fluoro-3,6-diiodo-benzene mol-ecule (r.m.s. deviation of all 12 atoms = 0.016 Å) and twisted 4-(pyridin-4-ylsulfan-yl)pyridine mol-ecule [dihedral angle between pyridyl rings = 54.88 (13)°] are connected by N⋯I inter-actions [2.838 (4) Å], generating a supra-molecular chain with a step-ladder topology. These chains are connected in the crystal by C-H⋯F and C-H⋯π(pyrid-yl) inter-actions.

| S-EPMC2983392 | biostudies-literature

4-(Anthracen-9-yl)-2-phenyl-6-(pyridin-2-yl)pyridine.

Project description:In the title compound, C(30)H(20)N(2), the anthracene ring system is approximately planar [maximum deviation = 0.035 (2) Å] and is nearly perpendicular to the central pyridine ring, making a dihedral angle of 75.73 (7)°. The terminal pyridine ring and the phenyl ring are oriented at dihedral angles of 8.11 (10) and 13.22 (10)°, respectively, to the central pyridine ring.

| S-EPMC3344146 | biostudies-literature

N,N'-Bis(pyridin-2-yl)benzene-1,4-dicarboxamide.

Project description:Mol-ecules of the title compound, C(18)H(14)N(4)O(2), are located around an inversion center and connected into chains in the crystal via inter-molecular N-H⋯N hydrogen bonds generating an R(2) (2)(8) motif.

| S-EPMC3050221 | biostudies-literature

4-(1H-Pyrrolo-[2,3-b]pyridin-2-yl)pyridine.

Project description:The asymmetric unit of the title compound, C12H9N3, contains two independent mol-ecules in which the dihedral angle between the pyridine and aza-indole rings are 8.23 (6) and 9.89 (2)°. In the crystal, both types of mol-ecule are connected by pairs of N-H-N hydrogen bonds into inversion dimers.

| S-EPMC3647869 | biostudies-literature

2-(1H-Pyrrolo-[2,3-b]pyridin-2-yl)pyridine.

Project description:In the title compound, C(12)H(9)N(3), the dihedral angle between the pyridine and aza-indole rings is 6.20 (2)°. In the crystal, pairs of N-H⋯N hydrogen bonds link mol-ecules into inversion dimers.

| S-EPMC3379496 | biostudies-literature

Hydrogen Evolution from Additive-Free Formic Acid Dehydrogenation Using Weakly Basic Resin-Supported Pd Catalyst.

Project description:Hydrogen, as a noncarbon energy source, plays a significant role in future clean energy vectors. However, concerns about the safe storage and transportation of hydrogen gas limit its wide application. Featured with high H2 volumetric density, nontoxicity, and nonflammability, formic acid (FA) is regarded as one of the most encouraging chemical hydrogen carriers. The search for heterogeneous catalysts with decent catalytic activity and stability for FA decomposition is one of the hottest research topics in this area. In this paper, three weakly basic resins with different functional groups, including D201 with -N+(CH3)3, D301 with -N(CH3)2, and D311 with -NH2, were investigated as alternative catalyst supports for Pd catalysts. The prepared basic resin-supported Pd catalysts were evaluated for the FA dehydrogenation reaction under atmospheric pressure and temperatures ranging from 30 to 70 °C. The results showed that the catalytic activity of the three different resin-supported Pd catalysts follows the order of Pd/D201 > Pd/D301 > Pd/D311. Particularly, a high turnover frequency value of 547.6 h-1 was achieved when employing Pd/D201 as the FA dehydrogenation reaction catalyst at 50 °C. The apparent activation energies for the three different Pd/resin catalysts were calculated, of which the Pd/D210 catalyst demonstrates the lowest activation energy of 42.9 kJ mol-1. The reasons for the superior catalytic behavior, together with the reaction mechanism, were then investigated and illustrated.

| S-EPMC9089338 | biostudies-literature

New Approach for the One-Pot Synthesis of 1,3,5-Triazine Derivatives: Application of Cu(I) Supported on a Weakly Acidic Cation-Exchanger Resin in a Comparative Study.

Project description:An efficient and simple methodology for Ullmann Cu(I)-catalyzed synthesis of di- and trisubstituted 1,3,5-triazine derivatives from dichlorotriazinyl benzenesulfonamide and corresponding nucleophiles is reported. Cations Cu(I) supported on macroporous and weakly acidic, low-cost industrial resin of polyacrylate type were used as a catalyst. The reaction times and yields were compared with traditional synthetic methods for synthesis of substituted 1,3,5-triazine derivatives via nucleophilic substitution of chlorine atoms in dichlorotriazinyl benzenesulfonamide. It was found that Ullmann-type reactions provide significantly shortened reaction times and, in some cases, also higher yields. Finally, trisubstituted s-triazine derivatives were effectively prepared via Ullmann-type reaction in a one-pot synthetic design. Six new s-triazine derivatives with potential biological activity were prepared and characterized.

| S-EPMC6804075 | biostudies-literature

6-Chloro-N-(pyridin-4-ylmeth-yl)pyridine-3-sulfonamide.

Project description:In the title sulfonamide derivative, C11H10ClN3O2S, the dihedral angle between the pyridine rings is 46.85 (12)°. The N atom of the chloro-pyridine ring is anti to the N-H bond. In the crystal, mol-ecules are linked through N-H⋯N hydrogen bonds into zigzag chains parallel to [001] with a C(7) graph-set motif.

| S-EPMC3885039 | biostudies-literature

2-Amino-benzoic acid-4-(pyridin-4-yl-disulfan-yl)pyridine (1/1).

Project description:The title 1:1 co-crystal, C(7)H(7)NO(2)·C(10)H(8)N(2)S(2), features a highly twisted 4-(pyridin-4-yldisulfan-yl)pyridine mol-ecule [dihedral angle between the pyridine rings = 89.06 (10)°]. A small twist is evident in the 2-amino-benzoic acid mol-ecule, with the C-C-C-O torsion angle being -7.7 (3)°. An N-H⋯O hydrogen bond occurs in the 2-amino-benzoic acid mol-ecule. In the crystal, mol-ecules are linked by O-H⋯N and N-H⋯N hydrogen bonds into a supra-molecular chain along the b axis. These are connected into layers by π-π inter-actions occurring between pyridine rings [centroid-centroid distance = 3.8489 (15) Å]. The layers are connected along the a axis by C-H⋯O contacts. The crystal studied was a racemic twin.

| S-EPMC3239006 | biostudies-literature

4-[(E)-2-(Pyridin-2-yl)ethen-yl]pyridine-terephthalic acid (2/1).

Project description:The title 2:1 co-crystal, 2C12H10N2·C8H6O4, crystallizes with one mol-ecule of 4-[(E)-2-(pyridin-2-yl)ethen-yl]pyridine (A) and one half-mol-ecule of terephthalic acid (B) in the asymmetric unit. In the crystal, the components are linked through heterodimeric COOH⋯Npyridine synthons, forming linear aggregates of composition -A-B-A-B-. Further linkage through weak C-H⋯O and C-H⋯π inter-actions gives two-dimensional hydrogen-bonded undulating sheets propagating in the [100] and [010] directions. These layers are connected through additional weak C-H⋯O contacts, forming a three-dimensional structure.

| S-EPMC3588979 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data