270589-02-1

Basic information

• Product Name: 1-dimethyl(2-pyridyl)silyl-2,2-diphenylethene
• Synonyms: 1-dimethyl(2-pyridyl)silyl-2,2-diphenylethene
• CAS NO: 270589-02-1
• Molecular Weight: 315.49
• Mol File: 270589-02-1.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1-dimethyl(2-pyridyl)silyl-2,2-diphenylethene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-dimethyl(2-pyridyl)silyl-2,2-diphenylethene(270589-02-1)
• EPA Substance Registry System: 1-dimethyl(2-pyridyl)silyl-2,2-diphenylethene(270589-02-1)

Safety Data

• Hazardous Substances Data: 270589-02-1(Hazardous Substances Data)

Upstream product

• 591-50-4 iodobenzene 
• 321155-39-9 dimethyl(2-pyridinyl)(vinyl)silane 
• 13737-04-7 2-(trimethylsilyl)pyridine 
• 21032-48-4 2-(dimethylhydrosilyl)pyridine 
• 108-86-1 bromobenzene 
• 119-61-9 benzophenone 
• 243468-48-6 bis(2-pyridyldimethylsilyl)methane 

Downstream Products

• 1450-63-1 1,1,4,4-tetraphenyl-1,3-butadiene 
• 55004-88-1 1-(4-(2,2-diphenylvinyl)phenyl)ethanone 

Relevant articles and documents

Stereoselective synthesis of multisubstituted butadienes through directed Mizoroki-Heck reaction and homocoupling reaction of vinyl(2-pyridyl)silane

(Chemical Equation Presented) We have developed the homocoupling reaction of alkenyl(2-pyridyl)silanes mediated by Cul and CsF, in which the strong directing effect of the 2-pyridyl group was observed. The homocoupling reaction was successfully integrated with the Mizoroki-Heck reaction of vinyl(2-pyridyl)-silane with aryl halides, enabling a rapid and stereoselective synthesis of multisubstituted butadienes. From a relatively small compound library, it was possible to detect a number of fluorescent butadienes with a wide range of fluorescence color variations (blue to reddish-orange).

Diversity-oriented synthesis of multisubstituted olefins through the sequential integration of palladium-catalyzed cross-coupling reactions. 2-Pyridyldimethyl(vinyl)silane as a versatile platform for olefin synthesis

A novel strategy for the diversity-oriented synthesis of multisubstituted olefins, where 2-pyridyldimethyl (vinyl)silane functions as a versatile platform for olefin synthesis, is described. The palladium-catalyzed Heck-type coupling of 2-pyridyldimethyl(vinyl)silanes with organic iodides took place in the presence of Pd2-(dba) 3/tri-2-furylphosphine catalyst to give β-substituted vinylsilanes in excellent yields. The Heck-type coupling occurred even with α- and β-substituted 2-pyridyldimethyl(vinyl)silanes. The one-pot double Heck coupling of 2-pyridyldimethyl(vinyl)silane took place with two different aryl iodides to afford β,β-diarylated vinylsilanes in good yields. The palladium-catalyzed Hiyama-type coupling of 2-pyridyldimethyl(vinyl)silane with organic halides took place in the presence of tetrabutylammonium fluoride to give di- and trisubstituted olefins in high yields. The sequential integration of Heck-type (or double Heck) coupling and Hiyama-type coupling produced the multisubstituted olefins in regioselective, stereoselective, and diversity-oriented fashions. Especially, the one-pot sequential Heck/Hiyama coupling reaction provides an extremely facile entry into a diverse range of stereodefined multisubstituted olefins. Mechanistic considerations of both Heck-type and Hiyama-type coupling reactions are also described.