84247-81-4

Upstream product

• 17891-78-0 2,2,6,6-tetramethyl-2,6-disila-3-heptene 
• 61518-50-1 1,3-bis(trimethylsilyl)prop-1-enyl-lithium 
• 41309-43-7 (2-bromovinyl)trimethylsilane 
• 17891-78-0 1,3-bis(trimethylsilyl)propene 
• 100-52-7 benzaldehyde 
• 16939-57-4 (E)-buta-1,3-dienylbenzene 
• 754-05-2 ethenyltrimethylsilane 
• 536-74-3 phenylacetylene 
• 13984-49-1 (phenylethynyl)zinc chloride 
• 92509-53-0 (E)-trimethyl(4-phenylbut-1-en-3-yn-1-yl)silane 
• 120764-58-1 (1E,3Z)-4-phenylthio-1-trimethylsilyl-1,3-butadiene 
• 42201-74-1 <β-(Trimethylsilyl)vinyl>magnesium bromide 

Relevant academic research and scientific papers

Aza-peterson olefinations: Rapid synthesis of (E)-alkenes

An aza-Peterson olefination methodology to access 1,3-dienes and stilbene derivatives from the corresponding allyl- or benzyltrimethylsilane is described. Silanes can be deprotonated using Schlosser's base and added to N -phenyl imines or ketones to directly give the desired products in high yields.

Ruthenium-Catalyzed Silylation of 1,3-Butadienes with Vinylsilanes

A novel method for the synthesis of 1-silyl-substituted 1,3-butadienes, based on [RuHCl(CO)(PCy3)2]-catalyzed silylative coupling of terminal (E)-1,3-dienes with vinylsilanes, is reported. The reaction provides a facile and straightf

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.

STEREOSPECIFIC SYNTHESIS OF (1E,3Z)-AND (1E,3E)-1-TRIMETHYLSILYL-1,3-DIENES BY MEANS OF SEQUENTIAL CROSS-COUPLING REACTIONS

A new synthesis of stereodefined 1-trimethylsilyl-1,3-dienes is described.The method is based on two sequential coupling reactions between Grignard reagents and the readily available (Z)-or (E)-1-bromo-2-phenylthioethene, in the presence of transition met

The Synthesis of Alkenes from Carbonyl Compounds and Carbanions α to Silicon. Stereoselective Synthesis of 1-Trimethylsilylbuta-1,3-dienes

Reactions of aldehydes with the 1,3-bis(trimethylsilyl)propenyl anion in the presence of magnesium bromide or trimethyl borate give stereoselectively the alcohols (2) which can be transformed stereospecifically to either (1E,3E)- or (1E,3Z)-1-trimethylsilylbuta-1,3-dienes.