115045-59-5

Upstream product

• 100-42-5 styrene 
• 50-00-0 formaldehyd 
• 3386-35-4 1-octyl p-toluenesulfonate 
• 4237-71-2 di-isoamylmagnesium 
• 629-27-6 1-Iodooctane 
• 67300-99-6 1-phenylethenylmagnesium bromide 
• 108-86-1 bromobenzene 
• 872-05-9 1-Decene 
• 591-50-4 iodobenzene 
• 111-83-1 1-bromo-octane 
• 2206-94-2 1-acetoxy-1-phenylethene 
• 71-43-2 benzene 
• 17049-49-9 octylmagnesium bromide 
• 98-86-2 acetophenone 

Relevant academic research and scientific papers

Generation of Alkylidenecarbenes from 1,1-Dibromoalk-1-enes by the Reaction with Samarium Diiodide in Hexamethylphosphoric Triamide-Benzene

Reaction of 1,1-dibromoalk-1-enes with samarium diiodide in benzene containing 10percent of hexamethylphosphoric triamide (HMPA) affords rearranged alkynes; generation of alkylidenecarbenes is probably involved.

Inter- or intramolecular carbometalation of nonactivated alkynes by zirconacyclopentanes in the presence of copper chloride

Five- and six-membered carbocyles 2 and 3 can be obtained from zirconacyclopentanes of type 1 by a novel carbometalation with nonactivated alkynes in the presence of CuCl (see reaction scheme).

Reductive Alkylation of Alkenyl Acetates with Alkyl Bromides by Nickel Catalysis

Catalytic alkylation of stable alkenyl C?O electrophiles is synthetically appealing, but studies to date have typically focused on the reactions with alkyl Grignard reagents. We report herein a cross-electrophile reaction of alkenyl acetates with alkyl bromides. This work has enabled a new method for the synthesis of aliphatic alkenes from alkenyl acetates to be established that can be used to add more structural complexity and molecular diversity with enhanced functionality tolerance. The method allows for a gram-scale reaction and modification of biologically active molecules, and it affords access to useful building blocks. Preliminary mechanistic studies reveal that the NiI species plays an essential role for the success of the coupling of these two reactivity-mismatched electrophiles.

Bimolecular vinylation of arenes by vinyl cations

Styrene derivatives can be easily synthesized from vinyl triflates and arenes under mild reaction conditions, using [Li][Al(OC(CF3)3)4] as a catalyst and LiHMDS as a base. This transformation is likely to involve a vinyl cation intermediate as an electrophile, which is corroborated by DFT calculations, deuterium-labeling and other control experiments. The use of an inert weakly coordinating anion is a decisive factor in this bimolecular vinylation process. This journal is

Triphosgene and DMAP as Mild Reagents for Chemoselective Dehydration of Tertiary Alcohols

The utility of triphosgene and DMAP as mild reagents for chemoselective dehydration of tertiary alcohols is reported. Performed in dichloromethane at room temperature, this reaction is readily tolerated by a broad scope of substrates, yielding alkenes preferentially with the (E)-geometry. While formation of the Hofmann products is generally favored, a dramatic change in alkene selectivity toward the Zaitzev products is observed when the reaction is carried out in dichloroethane at reflux.

Iron-Catalyzed Cross-Coupling of Alkenyl Acetates

Stable C-O linkages are generally unreactive in cross-coupling reactions which mostly employ more electrophilic halides or activated esters (triflates, tosylates). Acetates are cheap and easily accessible electrophiles but have not been used in cross-couplings because the strong C-O bond and high propensity to engage in unwanted acetylation and deprotonation. Reported herein is a selective iron-catalyzed cross-coupling of diverse alkenyl acetates, and it operates under mild reaction conditions (0 C, 2 h) with a ligand-free catalyst (1-2 mol%). Iron clad: Acetates are underutilized electrophiles in metal-catalyzed cross-coupling reactions because of the strong alkenyl C-O bond and their propensity to engage in unwanted reactions. Combination of a ligand-free low-valent Fe catalyst with nucleophilic organomagnesium reagents, low temperature, and short reaction times results in highly selective cross-couplings with alkenyl acetates.

Palladium-tetraphosphine catalysed heck reaction with simple alkenes: Influence of reaction conditions on the migration of the double bond

The Heck reaction of aryl halides with simple alk-1-enes is a powerful method for the synthesis of (E)-1-arylalk-1-ene derivatives. The major problem of this reaction is the palladium-catalysed migration of the carbon-carbon double bond along the alkyl ch

Cobalt(diamine)-catalyzed cross-coupling reaction of alkyl halides with arylmagnesium reagents: Stereoselective constructions of arylated asymmetric carbons and application to total synthesis of AH13205

A cobalt-diamine complex catalyzes the cross-coupling reactions of primary and secondary alkyl halides with aryl Grignard reagents. It is confirmed that oxidative addition of alkyl halide to cobalt proceeds via a radical process. Optically pure Ueno-Stork halo acetals undergo diastereoselective cross-coupling reactions, the products of which are transformed into optically active THF derivatives. A sequential radical cyclization/arylation reaction under cobalt catalysis provides extremely short access to a synthetic prostaglandin AH13205.

Zr-Catalyzed Electrophilic Carbomagnesation of Aryl Olefins. Mechanism-Based Control of Zr-Mg Ligand Exchange

(Formula Presented) The first examples of efficient electrophilic Zr-catalyzed carbomagnesations are disclosed, where in contrast to previous catalytic carbomagnesations the alkyl moiety of the electrophile is transferred (vs that of the Grignard reagent)

Synthesis of 1,1-Disubstituted Ethenes by Means of Sequential Cross-Coupling Reactions

A variety of 1-alkenes are synthesized in 63-91percent yields by means of sequential cross-coupling reactions of Grignard reagents with readily available or commercial starting materials, in the presence of transition-metal catalysts.