52713-62-9

Upstream product

• 6738-06-3 phenylethynylmagnesium bromide 
• 29777-16-0 2-methyl-2-propenylzinc bromide 
• 1458-98-6 2-methyl-3-bromo-1-propene 
• 536-74-3 phenylacetylene 
• 98-81-7 1-bromovinylbenzene 
• 107035-97-2 2,5-dimethyl-3-(1-methylethyl)-5-hexen-3-ol 
• 134306-62-0 2-(2-phenyl-2-oxoethylseleno)benzothiazole 
• 4747-13-1 α-methoxystyrene 
• 134306-68-6 2-(2-hydroxy-2-phenyl-4-methyl-4-pentenylseleno)benzothiazole 

Downstream Products

• 312322-33-1 (pentamethylcyclopentadienyl)(2-methyl-4-phenylpentadienyl)ruthenium(II) 

Relevant academic research and scientific papers

Selective Synthesis of Silacycles by Borane-Catalyzed Domino Hydrosilylation of Proximal Unsaturated Bonds: Tunable Approach to 1,n-Diols

The tris(pentafluorophenyl)boron-catalyzed domino hydrosilylation of substrates carrying unsaturated functionalities in a proximal arrangement is presented to produce silacycles. Excellent levels of efficiency and selectivity were achieved in the cyclization by the deliberate choice of the hydrosilane reagents. The key to successful cyclic hydrosilylation is the reactivity enhancement of the second intramolecular hydrosilylation by a proximity effect. Not only dienes but also enones, enynes, ynones and enimines readily afford medium-sized silacycles under convenient and mild conditions. The cyclization proceeds with acceptable diastereoselectivity mainly controlled by the conformational bias towards inducing additional stereogenic centers. The silacycles obtained from this reaction were converted to 1,n-diols or 1,n-amino alcohols upon oxidation, thus rendering the present cyclization a powerful tool for accessing synthetically valuable building blocks. (Figure presented.).

Gallium-mediated allyl transfer from bulky homoallyl alcohol to aldehydes or alkynes: Control of dynamic σ-allylgalliums based on retro-allylation reaction

A new method for the preparation and control of dynamic σ-allylgalliums is disclosed. Upon treatment with a Grignard reagent and gallium trichloride, bulky homoallyl alcohols undergo gallium-mediated retro-allylation reaction to provide σ-allylgallium reagents. The σ-allylgallium reagents generated were applied to carbonyl allylation. The retro-allylation reaction generates (Z)- and (E)-σ-crotylgalliums stereospecifically, starting from erythro- and threo-homoallyl alcohols, respectively. The stereochemically defined crotylgallium reagents effected stereoselective allylation of aldehydes. Allylgallation reaction of alkynes with the allylgallium reagents prepared by retro-allylation is also described.

Pd(OAc)2/P(cC6H11) 3-catalyzed allylation of aryl halides with homoallyl alcohols via retro-allylation

Allylations of aryl halides take place upon treatment of tertiary homoallyl alcohols with aryl halides in the presence of cesium carbonate and a palladium catalyst. The allylation reaction would consist of the following steps: (1) oxidative addition of ar

Regioselective allylgallation of terminal alkynes

The reactions of terminal alkynes with allylgallium reagents generated in situ from gallium and allyl bromides gave the corresponding 1,4-dienes in good yield via Markovnikov addition in THF at 70°C. The Royal Society of Chemistry 2005.

Allyl- And Benzylindium Reagents. Carboindation of Carbon-Carbon and Carbon-Nitrogen Triple Bonds

The reaction of unactivated simple terminal alkynes 1 with allylindiums in THF proceeded smoothly to give the corresponding allylation products 2 in good to high yields. This result is in marked contrast to that of the reaction carried out in DMF, where the allylation of unactivated alkynes was very sluggish. The allylic group of the reagent was attached to the internal carbon of the triple bond, and indium was attached to the less substituted terminal carbon, except for the case of TMS substituted acetylenes 1j and 1k in which the allyl group went to the less substituted carbon of the triple bond. The reaction of unactivated simple terminal and certain internal acetylenes with benzylindium in THF proceeded smoothly to afford the corresponding benzylation products 18 in good to high yields. The benzyl group was attached to the less substituted unhindered carbon of the triple bond, and indium was attached to the more sterically congested carbon. The reaction of activated nitriles 3 with allylindiums in THF at 70°C gave the corresponding allylationenamination products 4 in high to excellent yields. This reaction provides a useful method for the synthesis of highly functionalized enamines, which are not easily available via conventional methods. The mechanisms on the above three indation reactions are discussed.

Preparation of 1,4-Dienes from 2-(2-Hydroxyalkylseleno)benzothiazoles by the Reaction Involving Se -> O Azaaromatic Ring Rearrangement

The reactions of 2-(2-oxoalkylseleno)benzothiazoles with allylic Grignard reagents in the presence of BF3*OEt2 gave the corresponding 2-benzothiazoles which, on treatment with Ph3P and NaH, afforded 1,4-dienes in good to excellent yields.

A Versatile Synthesis of 1,4-Dienes: Use of Vinyl Ethers as Vinyl Cation Equivalents

The α,β-dibromo ethers 2, in situ generated from the vinyl ethers 1 and bromine, react with the allylsilanes 3 in the presence of ZnCl2 to give the β-bromo ethers 4.Treatment of 4 with Na in diethyl ether yields 1,4-dienes 5 in 62-79percent overall yield.Key Words: Enol ether / Allylsilane / Bromo ether / 1,4-Diene / Alkoxyalkylation

Preparation of 1,4-Dienes from 2-(2-Hydroxyalkylseleno)benzothiazoles by the Reaction involving Se->O Aza-aromatic Ring Rearragement

The reaction of 2-(acylmethylseleno)benzothiazoles with allylic Grignard reagents in the presence of BF3*OEt2 gave the corresponding 2-(2-hydroxyalkylseleno)benzothiazoles which, on treatment with NaH and Ph3P, afforded 1,4-dienes in good to excellent yields.