114701-81-4

Upstream product

• 917-64-6 methyl magnesium iodide 
• 72047-51-9 Trimethyl-[2-((E)-styryl)-[1,3]dithian-2-yl]-silane 
• 18178-59-1 (E)-1,2-bis(trimethylsilyl)ethene 
• 42599-24-6 E-styryl iodide 
• 79678-00-5 α-deutero-vinyltrimethylsilane 
• 754-05-2 ethenyltrimethylsilane 
• 100-42-5 styrene 
• 13683-41-5 1-bromo-1-(trimethylsilyl)ethene 
• 16722-09-1 trimethylsilyloxirane 
• 78782-27-1 4,4,5,5-tetramethyl-2-styryl-[1,3,2]dioxaborolane 
• 1450-14-2 1,1,1,2,2,2-hexamethyldisilane 
• 104516-09-8 1-phenylbuta-2,3-dien-1-ol 
• 1066-54-2 trimethylsilylacetylene 
• 75-77-4 chloro-trimethyl-silane 

Relevant academic research and scientific papers

Vinylidene Homologation of Boronic Esters and its Application to the Synthesis of the Proposed Structure of Machillene

Alkenyl boronic esters are important reagents in organic synthesis. Herein, we report that these valuable products can be accessed by the homologation of boronic esters with lithiated epoxysilanes. Aliphatic and electron-rich aromatic boronic esters provided vinylidene boronic esters in moderate to high yields, while electron-deficient aromatic and vinyl boronic esters were found to give the corresponding vinyl silane products. Through DFT calculations, this divergence in mechanistic pathway has been rationalized by considering the stabilization of negative charge in the C?Si and C?B bond breaking transition states. This vinylidene homologation was used in a short six-step stereoselective synthesis of the proposed structure of machillene, however, synthetic and reported data were found to be inconsistent.

Palladium-Catalyzed Silylation of 2,3-Allenols with Unactivated Disilanes: Access to 2-Silyl-1,3-butadienes and α-Silyl-β-hydroxy Vinylsilanes

Regioselective silylation of 2,3-allenols with disilanes was carried out under catalysis of Pd2dba3/P(o-MeOC6H4)3. In the presence of Cs2CO3, the reaction achieved 2-silyl-1,3-dienes. Reaction of 1-aryl-2,3-allenols gave the products with excellent Z/E selectivity and E-isomers as the major species. Reaction of α-alkylallenols or α-alkyl-α-aryl-allenols resulted in products with moderate Z/E selectivity and E-isomers are also major. Without a base, the reaction produced α-silyl-β-hydroxyl vinylsilanes, which were converted to 2-silyl-1,3-dienes upon treatment with Cs2CO3

Endo Selectivity in the (4 + 3) Cycloaddition of Oxidopyridinium Ions

The (4 + 3) cycloaddition of 2-trialkylsilyl-4-alkylbutadienes with an N-methyloxidopyridinium ion affords cycloadducts with high regioselectivity and excellent endo selectivity.

Syntheses of 2-silicon-substituted 1,3-dienes

A number of 2-silicon substituted 1,3-dienes have been prepared by one of three routes: 1) Reactions of 1,3-dienyl Grignard reagents with silyl electrophiles or silyl Grignard reagents with 1,3-dienyl electrophiles; 2) Hydrosilylation of enynes; 3) Enyne cross metathesis. The strengths and limitations of each preparative method are discussed.

COMPOUNDS AND COMPOSITIONS CONTAINING SILICON AND/OR OTHER HETEROATOMS AND/OR METALS AND METHODS OF MAKING AND USING THEM

The present invention relates to compounds, intermediates, compositions, and methods of making compounds and intermediates related to the compounds of Formula (I) and/or Formula (II) and/or Formula (III) and/or Formula (IV) and/or Formula (VI) and/or Formula (VII) as disclosed herein wherein the various substituents are as defined in the written description.

Heck coupling with nonactivated alkenyl tosylates and phosphates: Examples of effective 1,2-migrations of the alkenyl palladium(II) intermediates

(Chemical Equation Presented) What the Heck! A catalytic system composed of a Pd complex with a basic, hindered alkyl phosphine ligand is capable of promoting Heck coupling of nonactivated vinyl tosylates and phosphates with electron-deficient olefins. An unexpected 1,2-migration of the alkenyl Pd II intermediates (see Scheme) leads to the isomerized Heck coupling product.

Formation of 1-(Trimethylsilyl) 1,4-Dienes by Vinylation of Allyltrimethylsilane in the Presence of the Palladium(0)/Silver Salt System

The major products formed in palladium-catalyzed reactions of allyltrimethylsilane with vinyl iodides, in the presence of silver ion or with vinyl triflates are 1-(tri-methylsilyl) 1,4-dienes.In the absence of silver salts, only traces of these dienes are formed, and desilylation is predominant.Addition of silver salts enhances the reaction rate, suppresses the desilylation, and affects the isomer distribution.The isolated yields of the 1-(trimethylsilyl) 1,4-dienes are, in general, low owing to unfavourable regioselectivity in the reactions.

Unified synthesis of vinylsilanes and silylated butadienes. Nickel-catalyzed olefination and silylolefination of dithioacetals

A simple unified reaction has been developed in the syntheses of various vinylsilanes and silylated butadienes by the nickel-catalyzed coupling of dithioacetals with appropriate Grignard reagents. Reactions of 2-aryl-2-(trimethylsilyl)dithianes with MeMgI

Synthesis of 1-Trimethylsilyl 1,3-Dienes by the Palladium-Catalyzed Reaction of Trimethylvinylsilane with Vinyl Iodides/Silver Nitrate or Vinyl Triflates

A series of 1-trimethylsilyl 1,3-dienes has been synthesized by a palladium-catalyzed coupling of trimethylvinylsilane (1) either with vinyl halides in the presence of silver salts or alternatively with vinyl triflates.Apart from enhancing the rate of the

(E)-(2-Bromoethenyl)diisopropoxyborane. A New Building Block for (E)-Olefins

(E)-(2-Bromoethenyl)diisopropoxyborane is a useful precursor for the synthesis of (E)-olefins by the stepwise cross-coupling reaction with organozinc chlorides and then with organic halides in the presence of a base, both catalyzed by Pd complex.