139214-35-0

Upstream product

• 54731-27-0 1-p-methylphenyl-1-trimethylsiloxyethene 
• 1822-00-0 trimethylsilylmethyllithium 
• 13170-43-9 (trimethylsilyl)methylmagnesium chloride 
• 122-00-9 para-methylacetophenone 
• 18276-76-1 Phosphorsaeure-diethyl-1-(4-methylphenyl)vinyl-ester 
• 51270-89-4 1-(1-bromoethenyl)-4-methylbenzene 
• 766-97-2 4-n-methylphenylacetylene 
• 1344025-28-0 1-(p-tolyl)vinyl trifluoromethanesulfonate 
• 56637-45-7 2-methyl-2-(4-methylphenyl)-1,3-dithiane 
• 41159-08-4 2-methyl-2-(4-methylphenyl)-2-methyl-1,3-dithiolane 

Downstream Products

• 1448863-25-9 (1R)-1-phenyl-3-p-tolyl-3-buten-1-ol 
• 1448863-27-1 (1R)-1-m-tolyl-3-p-tolyl-3-buten-1-ol 
• 1448863-26-0 (1R)-1-(naphth-2-yl)-3-p-tolyl-3-buten-1-ol 
• 91176-32-8 1-methyl-4-(3-phenylprop-1-en-2-yl)benzene 
• 269-43-2 naphtho<2,3-d>-1,3-dioxole 
• 1009632-40-9 C₂₁H₂₀O₂ 
• 1009632-29-4 C₂₂H₂₄O₂ 
• 10103-06-7 2,3-dimethoxynaphthalene 

Relevant academic research and scientific papers

A Stereoselective Reductive Hosomi-Sakurai Reaction

A novel reductive variant of the classical Hosomi-Sakurai reaction is reported. This transformation hinges on a redox-neutral, stereoselective internal reduction event under mild conditions. This operationally simple reaction relies on readily available starting materials and leads to useful products in diastereoselectivities of up to 7:1. The versatility of this new method is demonstrated through the stereoselective one-step synthesis of an AChE inhibitor.

Silver-promoted cross-coupling of substituted allyl(trimethyl)silanes with aryl iodides by palladium catalysis

A ligand-free Pd-catalyzed cross-coupling of substituted allyl(trimethyl)silanes with aryl iodides enabled by silver salts was developed. This reaction delivered allylic arenes chemoselectively and regioselectively. The study suggested that the reaction might proceed through oxidative addition of ArI to Pd(0) followed by halide abstraction to give an electrophilic complex ArPdX, which further reacted with allyl(trimethyl)silanes via electrophilic addition/desilylation/reductive elimination to afford the allyl-aryl coupling products.

Pd-Catalyzed C(sp3)-C(sp2) cross-coupling of Y(CH2SiMe3)3(THF)2 with vinyl bromides and triflates

Pd-Catalyzed C(sp3)-C(sp2) cross-coupling of Y(CH2SiMe3)3(THF)2 with vinyl bromides and triflates has been developed for efficient synthesis of various allyltrimethylsilanes. The cross-coupling reaction was conducted at room temperature with low catalyst loading of either Pd(PPh3)4 or Pd(PPh3)2Cl2, and exhibited high efficiency and a broad substrate scope. In combination with the cross-coupling by the Lewis-acid catalyzed Hosomi-Sakurai reaction, a novel three-component one-pot cascade reaction was then accomplished to deliver homoallylic alcohols and ethers with high regioselectivity and diastereoselectivity. The three-component reaction defined the yttrium complex as a novel one-carbon synthon, which could either trigger bifunctionalization of alkenes or link two electrophiles and would find applications in organic synthesis.

Nickel catalyzed dealkoxylative Csp2-Csp3 cross coupling reactions - Stereospecific synthesis of allylsilanes from enol ethers

The application of cyclic and acyclic enol ethers as electrophiles in cross coupling reactions offers new possibilities for the preparation of functional compounds. A novel nickel catalyzed dealkoxylative cross coupling reaction allows access to structurally diverse allylsilanes and alcohol derivatives with high stereospecificity and in good yields under mild reaction conditions directly from the corresponding enol ethers.

Asymmetric counteranion-directed catalytic hosomi-sakurai reaction

Counteranion control enables the enantioselective, organo Lewis acid catalyzed Hosomi-Sakurai reaction of (hetero)aromatic aldehydes and allylsilanes using an easily handled disulfonimide precatalyst (see scheme). The key to the success of this system is to turn the usually undesired silylium ion catalysis into the desired catalytic regime and pair the cation with an enantiopure disulfonimide anion, thereby applying the concept of asymmetric counteranion-directed catalysis.

The Effect of the Ring Size of the Dithiolato Leaving Group on the Orientation of β-Elimination in the Nickel-catalysed Alkenation of Cyclic Dithioacetals with Me3SiCH2MgCl

The product distribution (allyl- vs. vinyl-silanes) of the reactions of dithioacetals derived from alkyl aryl ketones with Me3SiCH2MgCl surprisingly depends on ring size of the cyclic dithioacetals, the five-membered ring substrates affording allylsilane as the major product while the six-membered analogues yield vinylsilanes predominantly.These results indicate that the leaving group, dithiolato moiety, may remain coordinated to the metal centre during the course of the catalytic process.