Two convenient and high-yielding preparations of 6,6′-dimethyl-2,2′-bipyridine by homocoupling of 6-bromopicoline

Cassol, Tânia M.; Demnitz, F. W. J.; Navarro, Marcelo; Neves, Eduardo Almeida

doi:10.1016/s0040-4039(00)01310-1

Cited by 34 publications

(13 citation statements)

References 14 publications

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“…2-Bromo-6-picoline, [13] 6,6 -dimethyl-2,2 -bipyridine, [14] and tetrakis(acetonitrile)copper(i) hexafluorophosphate [15] were synthesized and purified according to the literature methods. 6,6 -Bis(chloromethyl)-2,2 -bipyridine was also synthesized by the literature method [10] but was purified by flash chromatography on silica (CHCl 3 as eluent).…”

Section: Methodsmentioning

confidence: 99%

Copper(I) Templated Synthesis of a 2,2´-Bipyridine Derived 2-Catenane: Synthetic, Modelling, and X-ray Studies

et al. 2009

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Following molecular modelling employing molecular mechanics and semi-empirical (PM3) calculations as an aid to ligand design, a new copper(i)-containing [2]-catenane has been prepared by the reaction of 6,6 -bis[(4 -formylphenoxy)methyl]-2,2 -bipyridyl with 1,6-hexanediamine in the presence of a copper(i) template, followed by in situ sodium borohydride reduction of the tetra-imine species generated. The corresponding [2]-catenane was obtained as a deep orange crystalline solid. The X-ray structure of this product along with that of the corresponding bis-dialdehyde precursor copper(i) complex have been determined. In the latter case, the structure is pre-organized for catenane formation. The new catenane appears to be the first example of a tetrahedral metal template product incorporating a bis-bipyridyl derivative core. Isolation of the metal-free [2]-catenane has also been achieved following treatment of the copper(i) catenane complex in dimethylsulfoxide with tetrabutylammonium cyanide.

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Section: Methodsmentioning

confidence: 99%

Copper(I) Templated Synthesis of a 2,2´-Bipyridine Derived 2-Catenane: Synthetic, Modelling, and X-ray Studies

et al. 2009

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“…Additionally, the quantitative use of cyanide can be avoided in this way. There are a variety of known coupling reactions that (directly or indirectly) form 6,6′‐dimethyl‐2,2′‐bipyridine from 2‐bromo‐6‐methylpyridine, including Stille coupling,18 electrosynthesis21 and reductive couplings based on Ni19,22 and Pd catalysts 21,23. We decided to employ the method described by Liao et al19 because of its simple handling and ligand‐free reaction conditions.…”

Section: Resultsmentioning

confidence: 99%

Na₂(smbipy) – A Bipyridine‐Derived Ligand with Chelating Sulfonate Tags and Its 3d Metal Complexes

Oelkers

2014

Eur J Inorg Chem

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The sulfonated bipyridine derivative disodium 6,6Ј-bis-(sulfonatomethyl)-2,2Ј-bipyridine [Na 2 (smbipy)] was synthesized, and its complexation behaviour towards divalent 3d metals in aqueous solution was explored. The complexes of late 3d metals [M(smbipy)(H 2 O) 2 ]·H 2 O (M = Co, Ni, Zn) and [Cu(smbipy)(H 2 O)] are sparingly soluble in water, and their crystal structures show fourfold equatorial coordination (κ 4 N,NЈ,O,OЈ) of the smbipy ligand. Ammonia-rich solutions of the Ni II and Cu II aqua complexes yield the decomplexation [a] 5838 products [Ni(NH 3 ) 6 ](smbipy), [Ni(NH 3 ) 5 (H 2 O)](smbipy) and [Cu(NH 3 ) 4 ](smbipy)·2H 2 O. Buffered solutions with a reduced ammonia content lead to [Ni(smbipy)(NH 3 ) 2 ] and [Cu(smbipy)(NH 3 ) 3 ]·2H 2 O, and the latter shows twofold coordination of the smbipy ligand through the nitrogen atoms only (κ 2 N,NЈ). When nearly quantitative amounts of ammonia are applied, two closely related complexes with the core motif [(smbipy)Cu(μ-OH) 2 Cu] form. Crystal structures of all complexes were obtained, and their features are discussed. Scheme 1. Examples of sulfonated ligands that do not show significant sulfonate binding towards metal centres.

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“…[36] The use of sacrificial anodes has allowed reactions to be conducted in undivided cells in either DMF or EtOH. [37,38] Thus, the system of [NiBr 2 (dpa)] and a stainless-steel anode led to 90% biaryl coupling for 4-bromofluorobenzene and 63% for 4-acetylbromobenzene. [39] Electroanalytical studies on aryl homocoupling with Ni II have reported [40,41] that they involve classical homogeneous catalytic processes: oxidative addition, reductive elimination, and ligand exchange (Scheme 2).…”

Section: ) Homocoupling Of Organic Halidesmentioning

confidence: 99%

Carbon−Carbon Bond Formation with Electrogenerated Nickel and Palladium Complexes

2003

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Two convenient and high-yielding preparations of 6,6′-dimethyl-2,2′-bipyridine by homocoupling of 6-bromopicoline

Cited by 34 publications

References 14 publications

Copper(I) Templated Synthesis of a 2,2´-Bipyridine Derived 2-Catenane: Synthetic, Modelling, and X-ray Studies

Copper(I) Templated Synthesis of a 2,2´-Bipyridine Derived 2-Catenane: Synthetic, Modelling, and X-ray Studies

Na₂(smbipy) – A Bipyridine‐Derived Ligand with Chelating Sulfonate Tags and Its 3d Metal Complexes

Carbon−Carbon Bond Formation with Electrogenerated Nickel and Palladium Complexes

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Two convenient and high-yielding preparations of 6,6′-dimethyl-2,2′-bipyridine by homocoupling of 6-bromopicoline

Cited by 34 publications

References 14 publications

Copper(I) Templated Synthesis of a 2,2´-Bipyridine Derived 2-Catenane: Synthetic, Modelling, and X-ray Studies

Copper(I) Templated Synthesis of a 2,2´-Bipyridine Derived 2-Catenane: Synthetic, Modelling, and X-ray Studies

Na2(smbipy) – A Bipyridine‐Derived Ligand with Chelating Sulfonate Tags and Its 3d Metal Complexes

Carbon−Carbon Bond Formation with Electrogenerated Nickel and Palladium Complexes

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Na₂(smbipy) – A Bipyridine‐Derived Ligand with Chelating Sulfonate Tags and Its 3d Metal Complexes