54015-96-2

Usage

Classification

Organic compound

Structure

Two pyridine rings with a methoxy group attached to one of the rings

Common Uses

Ligand in coordination chemistry, organic synthesis, and as a building block in the preparation of other chemical compounds

Applications

Research and industrial processes

Properties

Versatile compound with the ability to form complexes with various metal ions.

Upstream product

• 109-04-6 2-bromo-pyridine 
• 1628-89-3 2-methoxypyridine 
• 65007-00-3 pyridin-2-yl trifluoromethanesulfonate 
• 40473-07-2 6-bromo-2-methoxypyridine 
• 882521-96-2 pyridine-2-boronic acid N-phenyldiethanolamine ester 
• 182275-70-3 2-iodo-6-methoxypyridine 
• 13737-04-7 2-(trimethylsilyl)pyridine 
• 1227700-45-9 6-methoxy-2-pyridylboronic acid N-methyliminodiacetic acid ester 
• 109-09-1 2-chloropyridine 
• 2398-37-0 3-methoxyphenyl bromide 
• 51954-54-2 2-(p-tolylthio)pyridine 
• 10495-73-5 2-bromo-6-(pyridin-2-yl)pyridine 
• 124-41-4 sodium methylate 
• 24367-66-6 2-pyridinesulfinic acid sodium salt 

Relevant academic research and scientific papers

Efficient and regioselective access to bis-heterocycles via palladium- catalysed coupling of organostannanes and organozincates derived from C-6 lithiated 2-methoxypyridine

The efficient and regioselective synthesis of various bis-heterocyclic compounds was performed using a regioselective one-pot lithiation- transmetallation-cross-coupling of 2-methoxypyridine.

Platinum(II), palladium(II) and gold(III) adducts and cyclometalated derivatives of 6-methoxy-2,2′-bipyridine: A comparative study

Reaction of 6-methoxy-2,2′-bipyridine (bpy6OMe) with the electron-rich platinum(II) complex [Pt(Me)2(DMSO)2] gave the rollover cyclometalated complex [Pt(κ2-N,C-bpy6OMe-H) (Me) (DMSO)] under mild conditions. The occurrence of rollover cyclometalation was demonstrated by single crystal X-ray diffraction structure determination. In contrast, reaction of bpy6OMewith [Pt(Ph)2(DMSO)2] and [Pt(Cl)2(DMSO)2] under mild conditions gave only adduct species of the type [Pt(X)2(bpy6OMe)] (X = Ph, Cl). Under harsher conditions, activation of a C-H bond in the methoxy substituent yielded the terdentate cyclometalated complex [Pt (κ3-N,N,C-bpy6OMe-H)Cl]. Finally, reaction of Pd(II) and Au(III) derivatives invariably gave adduct species, with the exception of the dimeric complex [Pd(κ2-N,C-bpy6OMe-H) (OAc)]2, which, however, was not isolated in pure form. The reactivity of bpy6OMe, as emerged from this study, was compared with that of the corresponding disubstituted ligand 6,6′-dimethoxy-2,2′-bipyridine, previously studied by us.

Stabilization and destabilization of the Ru-CO bond during the 2,2′-bipyridin-6-onato (bpyO)-localized redox reaction of [Ru(terpy)(bpyO)(CO)](PF6)

Two stereoisomers of [Ru(terpy)(bpyO)(CO)](PF6)([1]+ and [2]+; terpy = 2,2′:6′,2″-terpyridine, bpyO = 2,2′-bipyridin-6-onato) were prepared. The pyridonato moiety in the bpyO ligand of [1]+ and [2]+ is located trans and cis, respectively, to CO. Treatment of [1]+ and [2]+ with HPF6 produced [1H]2+ and [2H]2+, both of which contain bpyOH (bpyOH = 6-hydroxy-2,2′-bipyridine). The difference in the pKa values of [1H]2+ (3.5) and [2H]2+ (3.9) reflects the stronger electronic interaction between CO and the pyridonato moiety in the bpyO ligand in the trans position compared with that in the cis position. The molecular structures of [1](PF6), [2](PF 6)·H2O and [2H](PF6)2· 2H2O were determined by X-ray structure analyses. [1]+ and [2]+ undergo one, reversible reduction at E1/2 = -1.65 V and -1.51 V, respectively, and one irreversible reduction at Ep,c = -2.07 and Ep,c = -2.13 V, respectively. Both reductions are assigned to redox reactions localized at the terpy and bpyO ligands. Irreversible reduction of [1]0 results from reductive cleavage of the Ru-CO bond of [1]-. On the other hand, a two-electron oxidation of [2] - almost regenerates [2]+ because of the depression of the reductive Ru-CO bond cleavage of [2]- due to cyclometalation formed by an attack of oxygen of bpyO to the carbon of the Ru-CO bond. An unusually large shift of the ν(C≡O) band on going from [2]0 (1950 cm-1) to [2]- (1587 cm-1) also supports a reversible cyclometalation driven by the bpyO-localized redox reaction. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.

Rhodium(iii)-catalyzed switchable C-H acylmethylation and annulation of 2,2′-bipyridine derivatives with sulfoxonium ylides

A novel protocol for Rh(iii)-catalyzed switchable C-H acylmethylation and annulation of 2,2′-bipyridine derivatives with sulfoxonium ylides is reported. This protocol provides a facile approach to synthesize structurally diverse acylmethylated 2,2′-bipyridine derivatives and acyl pyrido[2,3-a]indolizines with a broad range of functional group tolerance.

New Access Routes to Privileged and Chiral Ligands for Transition-Metal Catalyzed Hydrogen Autotransfer (Borrowing Hydrogen), Dehydrogenative Condensation, and Alkene Isomerization Reactions

A group of transition-metal catalyzed hydrogen moving reactions, encompassing hydrogen autotransfer (HAT; also called borrowing hydrogen, BH), dehydrogenative condensation (DHC) and alkene isomerization, displays high atom economy and relies on widely ava

A novel approach for rhodium(iii)-catalyzed C-H functionalization of 2,2′-bipyridine derivatives with alkynes: A significant substituent effect

We described a novel approach for the C-H functionalization of 2,2′-bipyridine derivatives with alkynes. DFT calculations and experimental data showed a significant substituent effect at the 6-position of 2,2′-bipyridine, which weakened the adjacent N-Rh bond and provided the possibility of subsequent rollover cyclometalation, C-H activation, and functionalization.

Synthesis of Pyridylsulfonium Salts and Their Application in the Formation of Functionalized Bipyridines

An S-selective arylation of pyridylsulfides with good functional group tolerance was developed. To demonstrate synthetic utility, the resulting pyridylsulfonium salts were used in a scalable transition-metal-free coupling protocol, yielding functionalized bipyridines with extensive functional group tolerance. This modular methodology permits selective introduction of functional groups from commercially available pyridyl halides, furnishing symmetrical and unsymmetrical 2,2′- A nd 2,3′-bipyridines. Iterative application of the methodology enabled the synthesis of a functionalized terpyridine with three different pyridine components.

Structural and Synthetic Insights into Pyridine Homocouplings Mediated by a β-Diketiminato Magnesium Amide Complex

The reaction of [(DippNacnac)Mg(TMP)] (1) with 4-subtituted pyridines proceeds via sequential regioselective metallation and 1,2-addition to furnish a range of symmetric 4,4′-R2-2,2′-bipyridines in good yield, representing a new entry into bipyridine synthesis. Interestingly, the reaction of 1 with 2-OMe-pyridine led to formation of asymmetric bipyridine 6, resulting from the C6-magnesiation of the heterocycle followed by a C?C coupling step by addition to the C2 position of a second, non-metallated molecule, and subsequent elimination of [DippNacnacMgOMe]2 (7). Synthesis combined with spectroscopic and structural analysis help rationalise the underlying processes resulting in the observed reactivity, and elucidate the key role that the sterically encumbered β-diketiminate ligand plays in determining regioselectivity.

[Cu(P^P)(N^N)][PF6] compounds with bis(phosphane) and 6-alkoxy, 6-alkylthio, 6-phenyloxy and 6-phenylthio-substituted 2,2′-bipyridine ligands for light-emitting electrochemical cells

We report a series of [Cu(P^P)(N^N)][PF6] complexes with P^P = bis(2-(diphenylphosphino)phenyl)ether (POP) or 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (xantphos) and N^N = 6-methoxy-2,2′-bipyridine (MeObpy), 6-ethoxy-2,2′-bipyridine (EtObpy), 6-phenyloxy-2,2′-bipyridine (PhObpy), 6-methylthio-2,2′-bipyridine (MeSbpy), 6-ethylthio-2,2′-bipyridine (EtSbpy) and 6-phenylthio-2,2′-bipyridine (PhSbpy). The single crystal structures of all twelve compounds have been determined and confirm chelating modes for each N^N and P^P ligand, and a distorted tetrahedral geometry for copper(i). For the xantphos-containing complexes, the asymmetrical bpy ligand is arranged with the 6-substituent lying over the xanthene ‘bowl'. The compounds have been characterized in solution by1H,13C and31P NMR spectroscopies, and their photophysical and electrochemical properties are described. They are yellow emitters and solid samples show photoluminescence quantum yields in the range up to 38%, with emission lifetimes ≤10.2 μs. On going from powder to frozen Me-THF, the excited state lifetimes increase which might suggest the presence of thermally activated delayed fluorescence (TADF). All the compounds have been tested in light-emitting electrochemical cells (LECs). Bright and stable LECs are obtained with complexes containing alkoxy- or phenyloxy-substituted ligands, making this family of compounds very relevant for the future development of copper-based electroluminescent devices.

Csp2-Br bond activation of Br-pyridine by neophylpalladacycle: Formation of binuclear seven-membered palladacycle and bipyridine species

In this work, the synthesis and reactivity of seven-membered palladacycles are described, and a novel bi-pyridine synthesis in a catalytic pathway is reported. Neophyl-palladacycle(i) reacts with an excess of 2-Br-pyridine, giving the desired new binuclear seven-membered palladacycle (1) and unexpectedly, a bipyridine complex, [Pd(BiPy)Br2]. ESI-HRMS experiments show that fragmentation of the Pd-Br bond in 1 can take place producing unusual two coordinated Pd(ii) molecular ions, [Pd(NeoPyR)]+.