94879-58-0

Upstream product

• 25354-48-7 1-bromo-1-(p-methoxyphenyl)-2,2-diphenylethene 
• 127-09-3 sodium acetate 
• 18648-74-3 2,2-diphenyl-1-(4-methoxyphenyl)ethylene 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 24892-82-8 1-bromo-2-(1-phenylpropen-1-yl)benzene 
• 696-62-8 para-iodoanisole 
• 133627-94-8 10-bromo-3-methoxy-9-phenylphenanthrene 

Relevant academic research and scientific papers

Preparation method of fused ring compound

The invention discloses a preparation method of a fused ring compound III. The preparation method comprises the following step: in a solvent and in the presence of palladium acetate, alkali and a ligand, carrying out a reaction shown in the specification on a compound I and a compound II to obtain a compound III. The preparation method disclosed by the invention is relatively good in compatibilitywith a substrate, various polycyclic aromatic hydrocarbon compounds can be simply obtained in a short period of time through convergent synthesis, and particularly, heteroatom-containing polycyclic aromatic hydrocarbon shows extremely excellent regioselectivity.

Sequential Cross-Coupling/Annulation of ortho-Vinyl Bromobenzenes with Aromatic Bromides for the Synthesis of Polycyclic Aromatic Compounds

A sequential cross-coupling/annulation of ortho-vinyl bromobenzenes with aromatic bromides was realized, providing a direct and modular approach to access polycyclic aromatic compounds. A vinyl-coordinated palladacycle was proposed as the key intermediate for this sequential process. Excellent chemoselectivity and regioselectivity were observed in this transformation. The practicability of this method is highlighted by its broad substrate scope, excellent functional group tolerance, and rich transformations associated with the obtained products.

The photochemistry of 4-halobenzonitriles and 4-haloanisoles with 1,1-diphenyiethene in methanol. Homolytic cleavage versus electron-transfer pathways

The photochemical reactivity of a series of 4-halobenzonitriles and 4-haloanisoles with 1,1-diphenylethene in a nucleophilic solvent (methanol) has been investigated. Analysis of the photochemical reactions involving the 4-halobenzonitriles revealed formation of alkene-methanol adducts, such as 1-methoxy-2,2-diphenylethane, 1-methoxy-2,2-diphenylethene, and 1,1-dimethoxy-2,2-diphenylethane, indicative of a photochemical electron-transfer mechanism. These products were not significant in the photochemical reactions involving the 4-haloanisoles. Both the 4-halobenzonitriles and the 4-haloanisoles produced an 'arene-alkene-methanol Markovnikov adduct, 1-aryl-2-methoxy-2,2-diphenylethane (aryl = 4-cyanophenyl or 4-methoxyphenyl). This compound was shown to undergo an acid-catalysed elimination to 1-aryl-2,2-diphenylethene under the reaction conditions, which subsequently underwent a 6π-electrocyclization to the 3-substituted(cyano or methoxy)-9-phenylphenanthrene. Possible mechanisms for the observed reactivity are discussed and evaluated.

Photoreactivity of Some α-Arylvinyl Bromides in Acetic Acid. Selectivity toward Bromide versus Acetate Ions as a Mechanistic Probe

The photochemical reactions of four α-anisyl-β,β-diarylvinyl bromides (1a-1d), three α-phenyl-β,β-diarylvinyl bromides (1e-1g), and 9-(α-bromo-p-methoxybenzylidene)anthrone (2) in acetic acid in the presence of sodium acetate and tetraethylammonium bromide (labeled with 82Br) have been studied quantitatively. Bromide exchange, acetate formation, E/Z isomerization, an anisyl 1,2-shift, stilbene-type cyclization to phenanthrenes, reductive debromination, and oxidation are observed as primary pathways. For all compounds 1, nucleophilic substitution, accompanied by E/Z isomerization in both starting material and product with 1b,c and 1f,g and an anisyl 1,2-shift in 1e but not in 1f,g, is quite efficient and by far the most important process. (Quantum yields range from 0.1 to 0.3 as compared to 0.01-0.02 for cyclization and 0.001-0.01 for reduction). The α-anisylvinyl bromide 2 is virtually inert for photosubstitution. The selectivity constants toward bromide and acetate ions, corrected for their temperature dependence, the amounts of E/Z isomerized starting material and product, the occurrence or nonoccurrence of an anisyl 1,2-shift, and the nature of the capturing nucleophile in the acetolysis are all in quantitative agreement with the corresponding data for the thermal reactions of 1 in the same medium. The results strongly support a mechanism for the nucleophilic vinylic photosubstitution reactions that involves the generation of a product-forming intermediate, which is exactly the same as the intermediate formed in the thermal reaction, a "cold" (thermally relaxed) linear free vinyl cation.