Phenylethenyl-substituted silicones via Heck coupling reaction

Czech, Anna; Ganicz, Tomasz; Noskowska, Małgorzata; Stańczyk, Włodzimierz A.; Szeląg, Anna

doi:10.1016/j.jorganchem.2009.07.001

Cited by 4 publications

(3 citation statements)

References 27 publications

(35 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The crude product was purified by column chromatography using tetrahydrofuran and dichloromethane (20:80) as eluent which gave three stereoisomers of L 1 , namely the cis–trans–cis L 1A , cis–cis–trans L 1B and all- trans L 1C , in the respective 35%, 60%, and 5% compositions . Although there are several methods available for obtaining peripherally modified cyclotetrasiloxanes, the Heck-coupling reaction was found to be successful in this case exhibiting an excellent functional group tolerance and good stereochemical separation . It is worth noting that a single cyclic tetrasiloxane containing propylammonium trifluoromethanesulfonate and methyl side groups in cis–trans–cis geometry has been recently synthesized from the hydrolytic condensation of 3-aminopropyldiethoxymethylsilane …”

Section: Resultsmentioning

confidence: 99%

Stereochemically Distinct Cyclotetrasiloxanes Containing 3-Pyridyl Moieties and Their Functional Coordination Polymers

2016

View full text Add to dashboard Cite

Synthesis of new cyclotetrasiloxane scaffolds containing peripherally functionalized 3-pyridyl moieties, [MeSiO(CH═CH(3)Py)]4 (L(1)) and [MeSiO(CH2CH2(3)Py)]4 (L(2)), and their reactivity studies with certain d(10) metal ions are reported. The ligand L(1) is obtained by the Heck-coupling reaction of tetramethyl tetravinyl tetrasiloxane (D4(vi)) and 3-bromopyridine in the presence of the Pd(0) catalysts. The as-synthesized ligand L(1) shows the presence of three stereoisomers, cis-trans-cis (L(1A)), cis-cis-trans (L(1B)), and all-trans (L(1C)), which are quantitatively separated by column chromatography. Subsequent reduction of L(1A), L(1B), and L(1C) with triethylsilane in the presence of catalytic amounts of Pd/C leads to the formation of the ligands L(2A), L(2B), and L(2C) with retention of stereochemistry due to the precursor moieties. Treatment of ZnI2 with L(1A) gives a one-dimensional coordination framework [(L(1A))4(ZnI2)2]∞, 1. These 1D-chains are further connected by π-π stacking interactions between the pyridyl groups of the adjacent chains leading to the formation of a three-dimensional network with the topology of a PtS net. The reaction of silver nitrate with ligand L(1B) gives a chain like one-dimensional cationic coordination polymer {[(L(1B))4Ag2]·2NO3·H2O·CH3OH }∞, 2, consisting of two different kinds of 32-membered macrocycles. Treatment of the all-trans ligand L(2C) with copper(I) iodide salt results in the formation of a cubane-type Cu4I4 cluster MOF [(L(2C))4Cu4I4]∞, 3, in a two-dimensional 4-connected uninodal sql/Shubnikov tetragonal plane net topology represented by the Schläfli symbol {4(4).6(2)}. This MOF displays a thermochromic luminescence behavior due to Cu4I4 clusters showing an orange emission at 298 K and a blue emission at 77 K.

show abstract

Section: Resultsmentioning

confidence: 99%

Stereochemically Distinct Cyclotetrasiloxanes Containing 3-Pyridyl Moieties and Their Functional Coordination Polymers

2016

View full text Add to dashboard Cite

show abstract

“…Initial scoping studies employed a commercially-available dimethylvinylethoxysilane, ViMe2SiOEt, which was reacted with 2-bromonaphthalene to obtain a conjugated ethoxysilane by Heck coupling [52,53]. However, both E-and Z-stereoisomers were identified in the crude reaction product, which was obtained in low yield (14 %).…”

Section: Synthesis Of Ethoxydimethyl(2-naphthylethyl)silanementioning

confidence: 99%

Thiolated Janus Silsesquioxane Tetrapod: New Precursors for Functional Materials

et al. 2022

View full text Add to dashboard Cite

Herein, we report synthetic strategies for the development of a bifunctional Janus T4 tetrapod (Janus ring), in which the orthogonal silsesquioxane and organic faces are independently functionalized. An all-cis T4 tetrasilanolate was functionalized to introduce thiol moieties on the silsesquioxane face and naphthyl groups on the organic face to introduce luminescent and self-organization properties. The stepwise synthesis conditions required to prepare such perfectly defined oligomers via a suite of well-defined intermediates and to avoid polymerization or reactions over all eight positions of the tetrapod are explored via 29Si, 13C and 1H NMR, FTIR and TOF-ESI mass spectroscopy. To the best of our knowledge, this is one of the few reports of Janus T4 tetrapods, with different functional groups located on both faces of the molecule, thus expanding the potential range of applications for these versatile precursors.

show abstract

“…27 On the other hand, [PdCl(P{ p-Tol} 3 ) 2 SnCl 3 ] and [Pd 2 Cl 2 (P{ p-Tol} 3 ) 2 -(SnCl 3 ) 2 ] showed promising reactivity in the Heck-type arylation of vinylsiloxanes. 45 Scheme 45 Polymerization of alkynes.…”

Section: 'Co-sn' Catalyzed Organic Reactionsmentioning

confidence: 99%

Recent advances in heterobimetallic catalysis across a “transition metal–tin” motif

2015

View full text Add to dashboard Cite

Heterobimetallic catalysts, bearing a metal-metal bond between a transition metal (TM) and a tin atom, are very promising due to their ability in mediating a wide variety of organic transformations. Indeed the utilization of such catalysts is a challenging and evolving area in the field of homogeneous catalysis. Catalysis across a 'TM-Sn' motif is an emerging area in the broader domain of multimetallic catalysis. The present review apprises the chemists' community of the past, present and future scope of this versatile catalytic motif. The TM-Sn catalyzed reactions presented include, among others, Friedel-Crafts alkylation, carbonylation, polymerization, cyclization, olefin metathesis, Heck coupling, hydroarylation Michael addition and tandem coupling. The mechanistic aspects of the reactions have been highlighted as well.

show abstract

Phenylethenyl-substituted silicones via Heck coupling reaction

Cited by 4 publications

References 27 publications

Stereochemically Distinct Cyclotetrasiloxanes Containing 3-Pyridyl Moieties and Their Functional Coordination Polymers

Stereochemically Distinct Cyclotetrasiloxanes Containing 3-Pyridyl Moieties and Their Functional Coordination Polymers

Thiolated Janus Silsesquioxane Tetrapod: New Precursors for Functional Materials

Recent advances in heterobimetallic catalysis across a “transition metal–tin” motif

Contact Info

Product

Resources

About