77134-00-0

Upstream product

• 96000-21-4 1-(3-chloro-1-propenyl)-4-methylbenzene 
• 3333-13-9 p-allyltoluene 
• 64-19-7 acetic acid 
• 591-87-7 Allyl acetate 
• 127-08-2 potassium acetate 
• 77133-98-3 1-((1S,2R)-2-Bromo-cyclopropyl)-4-methyl-benzene 
• 624-31-7 4-tolyl iodide 
• 5720-05-8 4-methylphenylboronic acid 
• 15209-49-1 [di-(4-tolyl)]iodonium tosylate 
• 106-38-7 para-bromotoluene 
• 104-87-0 4-methyl-benzaldehyde 
• 97585-04-1 ethyl (E)-3-(4-methylphenyl)acrylate 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 1866-39-3 trans-p-methylcinnamic acid 

Downstream Products

• 62056-37-5 1-methyl-4-[(1E)-3-phenylprop-1-en-1-yl]benzene 
• 1514677-35-0 (R)-2-(4-methoxyphenyl)-5-methyl-5-((R)-1-(p-tolyl)allyl)oxazol-4(5H)-one 
• 164527-49-5 dimethyl (E)-2-(3-(4-methylphenyl)allyl)malonate 
• 1223575-31-2 (E)-1-chloro-4-(3-phenyl-allylsulfanyl)benzene 
• 94711-83-8 p-Methyl-cinnamyl-p-tolylether 
• 1175523-06-4 C₁₆H₁₅Cl 
• 1228050-59-6 C₁₇H₁₈ 
• 134539-87-0 1-methyl-4-(3-phenyl-1-propen-1-yl)benzene 

Relevant academic research and scientific papers

C–C Cross-Coupling Reactions of Organosilanes with Terminal Alkenes and Allylic Acetates Using PdII Catalyst Supported on Starch Coated Magnetic Nanoparticles

Starch coated magnetic nanoparticles supported palladium catalyst has been explored to perform C–C cross coupling reactions, such as oxidative Heck coupling and Tsuji–Trost allylic coupling using organosilicon compounds as one of the coupling partners. The biopolymer coated magnetic catalyst was very easy to recover magnetically and was efficiently recycled in the subsequent batches. All the reactions were performed in air and thus the necessity of air and moisture free reaction condition is avoided. The present protocols show wide substrate scope and good yields of the products.

Size-Exclusion Borane-Catalyzed Domino 1,3-Allylic/Reductive Ireland–Claisen Rearrangements: Impact of the Electronic and Structural Parameters on the 1,3-Allylic Shift Aptitude

The reductive Ireland–Claisen rearrangement through borane-mediated hydrosilylation is reported. The method employs a borane catalyst with a special structural design and affords access to synthetically relevant products with high diastereoselectivity. Depending on electronic and structural parameters, the reaction can be coupled with a 1,3-allylic shift, thus the valence isomer of the Ireland–Claisen product is formed.

Sequential Palladium-Catalyzed Allylic Alkylation/retro-Dieckmann Fragmentation Strategy for the Synthesis of α-Substituted Acrylonitriles

A straightforward synthesis of α-substituted acrylonitriles is described using 4-cyano-3-oxotetrahydro-thiophene (c-THT) as an acrylonitrile surrogate. This unprecedented two-step sequence featuring a palladium-catalyzed allylic alkylation (Pd-AA) and a retro-Dieckmann fragmentation provides a general entry into diversely substituted 1,4-dienes.

Hypervalent iodine initiated intramolecular alkene dimerisation: A stereodivergent entry to cyclobutanes

The emergence of new methods for the stereoselective synthesis of strained carbocycles is a challenging but worthwhile endeavour. Cyclobutanes, in particular, have attracted the attention of both medicinal chemists and material scientists for their unique properties. Herein, we present a new method that allows access to highly functionalized cyclobutanes with complementary all-trans and trans-cis-trans relative stereochemistry, that could not be accessed before. This approach consists of an intramolecular dimerisation of non-conjugated dienes using an oxidative single electron transfer (SET) process, and is initiated by catalytic amounts of hypervalent iodine reagents. The potential uses of these cyclobutanes is demonstrated with selective functionalization, including the formation of diols and carboxylic acids.

Highly Enantioselective, Base-Free Synthesis of α-Quaternary Succinimides through Catalytic Asymmetric Allylic Alkylation

The synthesis of diversely substituted five-membered ring succinimide derivatives is reported featuring a direct, base-free, palladium-catalyzed asymmetric allylic alkylation. The method allows a straightforward access to the desired heterocyclic scaffold bearing an all-carbon α-quaternary stereogenic center in high yields and good to excellent enantioselectivities. To further demonstrate the synthetic utility of the method, the allylated products were further converted to various versatile chiral building blocks, including a chiral pyrrolidine and a spirocyclic derivative, using selective transformations.

Hydrazone-Pd-catalyzed direct intermolecular reaction of: O -alkynylphenols with allylic acetates

We found that the hydrazone-Pd-catalyzed direct intermolecular reaction of o-alkynylphenols with allylic acetates afforded the corresponding 2-substituted-3-allylbenzofuran derivatives. This reaction proceeded smoothly at room temperature using a hydrazon

Ruthenium-Catalyzed Cross-Metathesis of Allyl Acetate and Styrenes: A Practical Approach to the Synthesis of Tripolinolate A and Its Analogs

The scope of the Ru-catalyzed cross-metathesis of allyl acetates and styrenes was explored. A variety of electronically and structurally divergent styrenes were tolerated, and the resultant products were obtained in reasonable yields. The reported method was utilized in the synthesis of inhibitors of the proliferation of glioma and colorectal cancer cells, tripolinolate A and its diacetate analog.

Stereoselective and Site-Specific Allylic Alkylation of Amino Acids and Small Peptides via a Pd/Cu Dual Catalysis

We report a stereoselective and site-specific allylic alkylation of Schiff base activated amino acids and small peptides via a Pd/Cu dual catalysis. A range of noncoded α,α-dialkyl α-amino acids were easily synthesized in high yields and with excellent enantioselectivities (up to >99% ee). Furthermore, a direct and highly stereoselective synthesis of small peptides with enantiopure α-alkyl or α,α-dialkyl α-amino acids residues incorporated at specific sites was accomplished using this dual catalyst system.

Terephthalic acid derived ligand-stabilized palladium nanocomposite catalyst for Heck coupling reaction: without surface-modified heterogeneous catalyst

A new protocol is reported for the synthesis of a heterogeneous palladium nanocomposite stabilized with a terephthalic acid-derived ligand (N,N-bis(4-hydroxy-3-methoxybenzylidene)terephthalohydrazide). This is a highly insoluble ligand in common organic solvents, except dimethylformamide and dimethylsulfoxide. The resulting palladium nanocomposite acts as an efficient catalyst precursor for Mizoroki–Heck coupling reactions conducted under various reaction conditions. The spectral data suggest that the rate, yield and recycling of the catalyst are more effective for C–C coupling reactions. Copyright

Pd-catalyzed oxidative olefination of arenes with olefins via C-H activation: Retention of the leaving group

Pd-catalyzed direct oxidative olefination of arenes with olefins via C-H activation is described in the absence of any chelating directing groups. For Pd-catalyzed oxidative coupling between arenes and allyl acetate, it was observed the retention of the leaving group.