17890-16-3

Usage

Chemical structure

2-[2-(Trimethylsilyl)ethyl]pyridine is a pyridine derivative with a trimethylsilyl group attached to the nitrogen atom.

Common uses

Used as a nucleophilic catalyst in organic reactions such as silylation of alcohols and phenols, as well as in the synthesis of pharmaceuticals and agrochemicals.

Catalytic properties

Efficiently catalyzes reactions under mild conditions.

Stability

Considered to be relatively stable and can be easily handled in a laboratory setting.

Upstream product

• 17082-69-8 2-trichlorosilylethylpyridine 
• 75-16-1 methylmagnesium bromide 
• 109-04-6 2-bromo-pyridine 
• 1066-54-2 trimethylsilylacetylene 
• 86521-05-3 2-(trimethylsilylethynyl)pyridine 
• 110-86-1 pyridine 
• 754-05-2 ethenyltrimethylsilane 
• 100-69-6 2-vinylpyridine 
• 75-77-4 chloro-trimethyl-silane 
• 111770-80-0 3-bromo-6-(trimethylsilylethynyl)pyridine 
• 109-06-8 α-picoline 
• 2344-80-1 Chloromethyltrimethylsilane 

Relevant academic research and scientific papers

Experimental and theoretical investigations into the manifestation of the γ-effect in 2- and 4-[2-silylethyl)]pyridines and pyridinium ions

The γ-effect of the group 14 metals is a stabilizing interaction involving the back-lobe of the σC-M (M = Si, Ge, Sn, Pb) interacting with the developing carbocation γ to the tetrel. This percaudal interaction has been observed in solvolysis experiments with significant rate enhancements over unsubstituted systems, and subsequent isolation of three-membered ring products. In this study, the γ-effect is experimentally investigated in the solid phase with X-ray crystallography, the solution phase with Si-C coupling constants, and the gas phase via collision-induced dissociation (CID). Moving from 2- and 4-silylethyl substituted pyridines to the more electron demanding substituted pyridinium ion systems results in systematic shifts in key structural parameters including the 29Si-13C NMR coupling constants consistent with the cyclopropane-like resonance form attributable to the γ-effect. However, these shifts are much less in magnitude than those previously reported for the well documented β-effect. The gas phase CID results also reflect this with the fragmentation pathways for the silylethyl substituted systems not being dominated by the percaudal interaction, compared to previous studies where all major fragments were attributable to the β-effect. Density functional theory (DFT) calculated hyperhomodesmotic equations in combination with natural bond orbital (NBO) theory also supported the experimental trends with the γ-effect providing stabilization in the pyridinium ion systems studied, but to a much smaller extent to the β-effect.

Rhodium Complexes Bearing PAlP Pincer Ligands

We report rhodium complexes bearing PAlP pincer ligands with an X-type aluminyl moiety. IR spectroscopy and single-crystal X-ray diffraction analysis of a carbonyl complex exhibit the considerable σ-donating ability of the aluminyl ligand, whose Lewis acidity is confirmed through coordination of pyridine to the aluminum center. The X-type PAlP-Rh complexes catalyze C2-selective monoalkylation of pyridine with alkenes.

Facile and highly selective silylation of vinylpyridines at the β-olefinic carbon by magnesium-promoted reduction

Magnesium-promoted reductive silylation of 2- and 4-vinylpyridines with chlorotrialkylsilanes in N-methylpyrrolidinone at room temperature led to the selective formation of a variety of the corresponding β-mono-silylated compounds at the terminal carbon atom in good to excellent yields, whereas silylation of 3-vinylpyridine under the same reduction conditions failed to give a complex mixture of silylated compounds. The difference of the results between 2- or 4-vinylpyridines and 3-vinylpyridine is attributed to that of the stabilizing effect to reaction intermediates by the resonance with the nitrogen atom of pyridine.

A Convenient Palladium-Catalyzed Coupling Approach to 2,5-Disubstituted Pyridines

2,5-Dibromopyridine has been found to undergo a regioselective palladium-catalyzed coupling reaction with terminal acetylenes and arylzinc halides to give the corresponding 2-alkynyl-5-bromo- and 2-aryl-5-bromopyridines, respectively, in 70percent-90percent isolated yields.To complement this chemistry, the triflate derived from 2-methyl-5-pyridinol was found to participate in a palladium-catalyzed reaction with terminal acetylenes leading to the corresponding 5-alkynyl-2-methylpyridines.These intermediates can be further manipulated to afford a broad range of 2,5-disubstituted pyridines.