Browse
Submit Data
Databases
API
Help

Dataset Information

39 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Substituted 2,2'-bipyridines by nickel-catalysis: 4,4'-di-tert-butyl-2,2'-bipyridine.

ABSTRACT: A simple, ligand-free synthesis of the important bipyridyl ligand 4,4'-di-tert-butyl-2,2'-bipyridine is presented. 5,5'-bis(trifluoromethyl)-2,2'-bipyridine is also synthesized by the same protocol. The syntheses efficiently couple the parent 2-chlorpyridies by a nickel-catalyzed dimerization with manganese powder as the terminal reductant.

SUBMITTER: Buonomo JA

PROVIDER: S-EPMC4160121 | biostudies-literature | 2013 Nov

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Substituted 2,2'-bipyridines by nickel-catalysis: 4,4'-di-<i>tert</i>-butyl-2,2'-bipyridine.

Buonomo Joseph A JA Everson Daniel A DA Weix Daniel J DJ

Synthesis 20131101 22

A simple, ligand-free synthesis of the important bipyridyl ligand 4,4'-di-<i>tert</i>-butyl-2,2'-bipyridine is presented. 5,5'-bis(trifluoromethyl)-2,2'-bipyridine is also synthesized by the same protocol. The syntheses efficiently couple the parent 2-chlorpyridies by a nickel-catalyzed dimerization with manganese powder as the terminal reductant. ...[more]

PMID: 25221358

Similar Datasets

4,4'-Di-tert-butyl-2,2'-bipyridine.

Project description:In the title compound, C(18)H(24)N(2), the mol-ecular unit adopts a trans conformation around the central C-C bond [N-C-C-N torsion angle of 179.2?(3)°], with the two aromatic rings almost coplanar [dihedral angle of only 0.70?(4)°]. The crystal packing is driven by co-operative contacts involving weak C-H?N and C-H?? inter-actions, and also the need to fill effectively the available space.

| S-EPMC2977408 | biostudies-literature

4,4'-Di-tert-butyl-2,2'-dipyridinium dichloride.

Project description:In the title compound, C(18)H(26)N(2) (2+)·2Cl(-), the complete dication is generated by crystallographic inversion symmetry; both N atoms are protonated and engaged in strong and highly directional N-H?Cl hydrogen bonds. Additional weak C-H?Cl contacts promote the formation of a tape along ca. [110]. The crystal structure can be described by the parallel packing of these tapes. The crystal studied was a non-merohedral twin with twin law [-1 0 0, 0 -1 0, -0.887 0.179 1] and the final BASF parameter refining to 0.026?(2) .

| S-EPMC3212297 | biostudies-literature

(4,4'-Di-tert-butyl-2,2'-bipyridine-?N,N')bis-(nitrato-?O,O')copper(II).

Project description:In the crystal of the title compound, [Cu(NO(3))(2)(C(18)H(24)N(2))], the Cu(II) ion is coordinated by two N atoms of the bipyridine ligand and four O atoms from the two nitrate anions in a distorted octahedral fashion. The dihedral angle between the planes of the two pyridine rings is 11.52?(10)°. In the crystal structure, weak C-H?O inter-actions may help to establish the packing.

| S-EPMC2968272 | biostudies-literature

?-Oxido-bis-[chlorido(4,4'-di-tert-butyl-2,2'-bipyridine-?N,N')dioxido-molybdenum(VI)] 0.2-hydrate.

Project description:The title hydrate, [Mo(2)Cl(2)O(5)(C(18)H(24)N(2))(2)]·0.2H(2)O, has been isolated as the oxidation product of [Mo(?(3)-C(3)H(5))Cl(CO)(2)(di-t-Bu-bipy)] (where di-t-Bu-bipy is 4,4'-di-tert-butyl-2,2'-bipyridine). A ?-oxide ligand bridges two similar MoCl(di-t-Bu-bipy)O(2) units, having the terminal oxide ligands mutually cis, and the chloride and ?-oxide trans to each other. In the binuclear complex, the coordination geometries of the metal atoms can be described as highly distorted octa-hedra. Individual complexes co-crystallize with a partially occupied water mol-ecule of crystallization (occupancy factor = 0.20; H atoms not located), with the crystal packing being mediated by the need to effectively fill the available space. A number of weak C-H?O and C-H?Cl inter-actions are present.

| S-EPMC3238648 | biostudies-literature

4,4'-Di-tert-butyl-2,2'-[imidazolidine-1,3-diylbis(methyl-ene)]diphenol.

Project description:In the title compound, C25H36N2O2, the two tert-butyl-substituted benzene rings are inclined at an angle of 53.5?(3)° to one another. The imidazolidine ring has an envelope conformation with with one of the C atoms of the ethylene fragment as the flap. The structure displays two intra-molecular O-H?N hydrogen bonds that generate S(6) ring motifs. The crystal studied was a non-merohedral twin with a fractional contribution of 0.281(6) for the minor domain.

| S-EPMC3770425 | biostudies-literature

1,1'-Di-tert-butyl-2,2',3,3',4,4',5,5'-octa-ethyl-1,1'-bis-tannole.

Project description:The title compound, [Sn(2)(C(4)H(9))(2)(C(12)H(20))(2)], has two 1-stannacyclo-penta-diene skeletons related by inversion symmetry located at the mid-point of the Sn-Sn bond [2.7682 (2) Å]. Thus, the asymmetric unit comprises one half-mol-ecule. The planarity of the stannacyclo-penta-diene ring is illustrated by the dihedral angle of 0.3 (1)°, defined by the C(4) and C-Sn-C planes. To avoid steric repulsion, the two stannole rings are oriented in an anti fashion through the Sn-Sn bond. These structural features are similar to those of other bis-tannoles.

| S-EPMC3152095 | biostudies-literature

Di-tert-butyl 2,2'-[(biphenyl-4,4'-diyl)-dioxy]diacetate.

Project description:The complete molecule of the title compound, C(24)H(30)O(6), is generated by a crystallographic inversion centre. In the unique part of the mol-ecule, the four-atom -O-CH(2)-C(= O)-O- chain between the benzene ring and the tert-butyl group assumes a zigzag conformation [O-C-C-O torsion angle = -162.3?(1)°].

| S-EPMC3006834 | biostudies-other

Tris(4,4'-di-tert-butyl-2,2'-bipyridine-?N,N')molybdenum(II) ?(6)-oxido-dodeca-?(2)-oxido-hexa-oxidohexa-molybdate(VI) acetonitrile tetra-solvate.

Project description:The asymmetric unit of the title compound, [Mo(C(18)H(24)N(2))(3)][Mo(6)O(19)]·4CH(3)CN, comprises an [Mo(di-t-Bu-bipy)(3)](2+) cation (di-t-Bu-bipy is 4,4'-di-tert-butyl-2,2'-bipyridine), two halves of Lindqvist-type [Mo(6)O(19)](2-) anions (with each anion completed by the application of a center of inversion) and four acetonitrile solvent mol-ecules. The geometry around the metal atom of the cation resembles a distorted octa-hedron, with each of the three di-t-Bu-bipy ligands being almost planar [deviation from planarity < 6.3?(2)°]. Supra-molecular inter-actions, namely Mo=O??, C N??, C-H?O and C-H?N, along with electrostatic forces, mediate the crystal packing. Two of the tert-butyl groups are affected by rotational disorder which was modeled over two distinct positions with major site occupancies of 0.707?(9) and 0.769?(8).

| S-EPMC3238728 | biostudies-literature

Di-tert-butyl (1,1'-binaphthyl-2,2'-di-oxy)diacetate.

Project description:In the crystal structure of the title compound, C(32)H(34)O(6), the mol-ecule is located on a twofold rotation axis. The two naphthyl fused-ring systems are aligned at 72.6 (1)°. Weak intermolecular C-H⋯O hydrogen bonding is present in the crystal structure.

| S-EPMC2968877 | biostudies-literature

Di-chlorido-(4,4'-di-tert-butyl-2,2'-bi-pyridine-?(2) N,N')palladium(II) dimethyl sulfoxide monosolvate monohydrate.

Project description:The title compound, [PdCl2(C18H24N2)]·(CH3)2SO·H2O, the Pd(II) ion is in a distorted square-planar geometry. The Pd-N bond distances are 2.022?(2) and 2.027?(2)?Å, the Pd-Cl bond distances are 2.2880?(7) and 2.2833?(7)?Å, and the ligand bite angle is 80.07?(9)°. The dimethyl sulfoxide and water mol-ecules form linear chains along [100] by O-H?O and O-H?S hydrogen bonds, generating eight- and 12-membered rings. C-H?Cl inter-actions link the chains, forming a three-dimensional arrangement. In addition, the 4,4-di-tert-butyl-2,2'-bi-pyridine ligand exhibits ?-? stacking inter-actions [centroid-centroid distances = 3.8741?(15) and 3.8353?(15)?Å]. The DMSO solvent is disordered and was refined with an occupancy ratio of 0.866?(3):0.134?(3).

| S-EPMC4051021 | 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