84751-16-6

Upstream product

• 41309-43-7 (2-bromovinyl)trimethylsilane 
• 78389-87-4 ((trimethylsilyl)ethynyl)zinc(II) chloride 
• 1066-54-2 trimethylsilylacetylene 
• 41309-43-7 (2-bromovinyl)trimethylsilane 

Downstream Products

• 142608-34-2 (E,E)-2-dimethylphenylsilyl-1,4-bis(trimethylsilyl)-1,3-butadiene 

Relevant academic research and scientific papers

Selective Oligomerization and [2 + 2 + 2] Cycloaddition of Terminal Alkynes from Simple Actinide Precatalysts

A catalyzed conversion of terminal alkynes into dimers, trimers, and trisubstituted benzenes has been developed using the actinide amides U[N(SiMe3)2]3 (1) and [(Me3Si)2N]2An[κ2-(N,C)-CH2Si(CH3)N(SiMe3)] (An = U (2), Th (3)) as precatalysts. These complexes allow for preferential product formation according to the identity of the metal and the catalyst loading. While these complexes are known as valuable precursors for the preparation of various actinide complexes, this is the first demonstration of their use as catalysts for C-C bond forming reactions. At high uranium catalyst loading, the cycloaddition of the terminal alkyne is generally preferred, whereas at low loadings, linear oligomerization to form enynes is favored. The thorium metallacycle produces only organic enynes, suggesting the importance of the ability of uranium to form stabilizing interactions with arenes and related π-electron-containing intermediates. Kinetic, spectroscopic, and mechanistic data that inform the nature of the activation and catalytic cycle of these reactions are presented. (Chemical Equation Presented).

A straightforward synthesis of symmetrical polyendiynes by dimerization reactions of silyl derivatives

A straightforward synthesis of polyendiynes is described. The method is based upon a simple dimerization reaction of silylated enynes in the presence of copper salts. A variety of polyunsaturated compounds have been obtained in high yields and with high retention of configuration.

A straightforward synthesis of substituted cyclopentenones

A new synthetic approach to substituted silylated cyclopentenones has been developed, starting from an easily accessible bis-silylated conjugated dienyne and based upon the reactions with unsaturated acyl chlorides.

PALLADIUM-CATALYZED DIASTEREOSELECTIVE SYNTHESES OF (E)-1-TRIMETHYLSILYL-2-ALKENES, (E)-1-TRIMETHYLSILYL-1-ALKEN-3-YNES, (1E,5E)-1-TRIMETHYLSILYL-1,5-ALKADIEN-3-YNES, (1E,3Z)- AND (1E,3E)-1-TRIMETHYLSILYL-1,3-ALKADIENES

On the basis of our observation that (E)-1-bromo-1-alkenes undergo preferentially stereospecific Pd-catalyzed cross-couplings with a variety of organometallics, in the presence of the corresponding (Z)-stereoisomers, efficient and convenient diastereoselective procedures have been developed to prepare nearly stereoisomerically pure (E)-1-trimethylsilyl-2-alkenes (4), (E)-1-trimethylsilyl-1-alken-3-ynes (5), (1E,5E)-1-trimethylsilyl-1,5-alkadien-3-ynes (6), and (1E,3E)-1-trimethylsilyl-1,3-alkadienes (8) from stereoisomeric mixtures of alkenyl bromides.Compounds 5 have been stereoselectively converted into (1E,3Z)-1-trimethylsilyl-1,3-dienes (7) by selective hydrometallations, followed by hydrolysis.Some synthetic applications of compounds 5-8 have been also examined.

HIGHLY DIASTEREOSELECTIVE SYNTHESIS OF (E)-1-TRIMETHYLSILYL-1-EN-3-YNES, (1E,3Z)- and (1E,3E)-1-TRIMETHYLSILYL-1,3-DIENES

In the stereospecific palladium-catalysed cross-coupling reaction of 1-alkynylzinc chlorides or (E)-1-alkenyl diisobutylalanes, (E)-2-bromovinyltrimethylsilane reacts preferentially, in the presence of the corresponding (Z)-stereoisomer to afford good yields of (E)-1-trimethylsilyl-1-en-3-ynes (4) or (1E,3E)-1-trimethylsilyl-1,3-dienes (6),respectively, having very high stereoisomeric purities.Compounds 4 are easily converted into (1E,3Z)-1-trimethylsilyl-1,3-dienes (5) by selective hydrometallation reactions, followed by protonolysis.