109898-18-2

Upstream product

• 187737-37-7 propene 
• 87802-71-9 (E)-methyl cinnamyl carbonate 
• 762-72-1 allyl-trimethyl-silane 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 853955-63-2 (E)-[2-(hydroxymethyl)phenyl]-dimethyl-(2-phenylethenyl)-silane 
• 107-05-1 3-chloroprop-1-ene 
• 563-47-3 3-Chloro-2-methylpropene 
• 536-74-3 phenylacetylene 
• 135068-04-1 allyldimethyl[(E)-2-phenylethen-1-yl]silane 
• 39491-73-1 (E)-(4-methylpenta-1,3-dien-1-yl)benzene 
• 104-55-2 3-phenyl-propenal 
• 119441-91-7 prop-1-en-2-ylzinc(II) chloride 
• 6783-05-7 trans-2-phenylvinylboronic acid 
• 513-42-8 3-hydroxy-2-methyl-1-propene 

Relevant academic research and scientific papers

Microwave-enhanced cross-coupling of allyl chlorides with vinyltrifluoroborates

The allylation of potassium alkenyltrifluoroborates with allyl chloride via a palladium catalyzed cross-coupling reaction occurs rapidly under microwave irradiation. The allylation reaction produces 1,4-pentadienes in high yields.

Cross-coupling synthesis of methylallyl alkenes: Scope extension and mechanistic study

Cross-coupling reactions between 2-methyl-2-propen-1-ol and various boronic acids are used to obtain aromatic-(2-methylallyl) derivatives. However, deboronation or isomerization side reactions may occur for several boronic acids. We describe herein the synthesis of original alkenes with good yields under mild reaction conditions that decrease these side reactions. The scope of this environmentally benign reaction is thereby extended to a wide variety of boronic acids. A mechanistic study was conducted and suggested a plausible catalytic cycle mechanism, pointing to the importance of the Lewis acidity of the boronic acid used.

Copper(I)-catalyzed alkylation of aryl- and alkenylsilanes activated by intramolecular coordination of an alkoxide

Let's coordinate: Copper(I)-catalyzed cross-coupling of alkenyl- and arylsilanes with primary alkyl iodides as well as allylic and benzylic halides as C(sp3)-X electrophilic coupling partners has been realized by intramolecular activation through alkoxide coordination. This alkylation tolerates a range of functional groups including a free hydroxy group. IPr=1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene. Copyright

Contra-Thermodynamic Positional Isomerization of Olefins

A light-driven method for the contra-thermodynamic positional isomerization of olefins is described. In this work, stepwise PCET activation of a more substituted and more thermodynamically stable olefin substrate is mediated by an excited-state oxidant an

Nickel-Catalyzed Cross-Coupling of Allyl Alcohols with Aryl- or Alkenylzinc Reagents

Nickel-catalyzed cross-coupling of allyl alcohols with aryl- and alkenylzinc chlorides through C-O bond cleavage was performed. Reaction of (E)-3-phenylprop-2-en-1-ol and 1-aryl-prop-2-en-1-ols with aryl- or alkenylzinc chlorides gave linear cross-coupling products. Reaction of 1-phenyl- or 1-methyl-substituted (E)-3-phenylprop-2-en-1-ol with aryl- or alkenylzinc chlorides resulted in 3-aryl/alkenyl-substituted (E)-(prop-1-ene-1,3-diyl)dibenzenes or 3-aryl/alkenyl-substituted (E)-(but-1-enyl)benzene. Reaction of allyl alcohol with p-Me2NC6H4ZnCl resulted in a mixture of normal coupling product 4-allyl-N,N-dimethylaniline and its isomerized product N,N-dimethyl-4-(prop-1-en-1-yl)aniline.

Nickel-catalyzed allylic substitution of simple alkenes

This report describes a nickel-catalyzed allylic substitution process of simple alkenes whereby an important structural motif, a 1,4-diene, was prepared. The key to success is the use of an appropriate nickel-phosphine complex and a stoichiometric amount of silyl triflate. Reactions of 1-alkyl-substituted alkenes consistently provided 1,1-disubstituted alkenes with high selectivity. Insight into the reaction mechanism as well as miscellaneous application of the developed catalytic process is also documented.

Nickel-catalyzed allylic substitution of simple alkenes

Nickel-catalyzed intermolecular allylic substitution of simple alkenes (ethylene and alpha olefins) is described. This method is the first catalytic intermolecular process for direct allylation of nonconjugated, nonstrained simple alkenes. Catalyst loadings as low as 2.5 mol % Ni afford the desired product in high yield in both gram-scale and smaller scale coupling reactions.

Palladium-catalyzed cross-coupling reactions of potassium alkenyltrifluoroborates with organic halides in aqueous media

Potassium vinyl and alkenyltrifluoroborates are cross-coupled with aryl and heteroaryl bromides using 1 mol % Pd loading of 4-hydroxyacetophenone oxime derived palladacycle or Pd(OAc)2 as precatalysts, K 2CO3 as base, and TBAB as additive and water reflux under conventional or microwave heating to afford styrenes, stilbenoids, and alkenylbenzenes. These borates can be cross-coupled diastereoselectively with allyl and benzyl chlorides using KOH as base in acetone-water (3:2) at 50°C and 0.1 mol % Pd loading, giving the corresponding 1,4-dienes and allylarenes, respectively. These simple phosphine-free reaction conditions allow the palladium recycling from the aqueous phase during up to five runs by extractive separation of the products, which contain 58-105 ppm of Pd.

Aminium Salts Induced Desulphurization of Allyl and Diallyl Thiiranes. Synthesis of Dienes and Trienes

Catalytic amounts of aminium salts A-B induce the conversion of methylene chloride in solutions of several allyl and diallyl episulphides 1-6 into the corresponding unsaturated derivatives 7-12.The desulphurization process, which occurs through a plausible chain electron-transfer mechanism, rapid and may proceed in a fashion that preserves the stereochemistry of the starting episulphide.

Syntheses of 1,3- and 1,4-Dienes by the Oxidative Coupling of 1-Alkenylstannanes and 2-Alkenylstannanes in the Presence of Palladium Catalyst

Treatment of 1-alkenylstannanes with tBuOOH in the presence of palladium catalyst gives 1,3-dienes.Cross coupling reaction between 1-alkenylstannanes and 2-alkenylstannanes provides 1,4-dienes selectively in good yields.