54046-74-1

Upstream product

• 100-42-5 styrene 
• 833-81-8 (E)-1,2-diphenylpropene 
• 13047-06-8 o-bromobenzophenone 
• 899425-05-9 2-bromo-N-methoxy-N-methylbenzamide 
• 88-65-3 2-bromobenzoic-acid 
• 7154-66-7 2-bromobenzoic acid chloride 
• 530-48-3 1,1-Diphenylethylene 
• 98-83-9 isopropenylbenzene 
• 673-32-5 1-Phenylprop-1-yne 
• 24892-81-7 1-(o-chlorophenyl)-1-phenylethylene 
• 24892-82-8 1-bromo-2-(1-phenylpropen-1-yl)benzene 
• 599-67-7 1,1-diphenylethanol 
• 89530-34-7 1-phenyl-3-trimethylsilylprop-2-yn-1-ol 

Relevant academic research and scientific papers

Direct Synthesis of Napthalenes by Nickel-Catalyzed Cascade Cyclization of o-Vinyl Chlorobenzenes with Internal Alkynes

An efficient nickel-catalyzed arylnickelation of alkyne/Heck cyclization of challenging o-vinyl chlorobenzenes with internal alkynes has been developed. This protocol enables synthesis of a wide variety of substituted naphthalenes in a cascade process from readily available starting materials. Mechanistic studies indicate the radical pathway is not involved in the cascade catalytic system.

Electrochemical [4+2] Annulation-Rearrangement-Aromatization of Styrenes: Synthesis of Naphthalene Derivatives

We report the first electrochemical strategy to synthesize functionalized naphthalene derivatives through [4+2] annulation—rearrangement–aromatization from styrenes under mild conditions. The electrolysis does not require metals, oxidants and high valence substrates, indicating the atom and step-economy ideals. The dehydrodimer produced through [4+2] cycloaddition of 4-methoxy α-methyl styrene is isolated and proved to be the key intermediate for the following oxydehydrogenation to form carbon cation, which undergoes rearrangement–aromatization to afford the final products. This reaction represents a powerful access to construct multi-substituted naphthalene blocks in a single step.

Synthesis of Substituted Naphthalenes by 1,4-Palladium Migration Involved Annulation with Internal Alkynes

The palladium catalyzed annulation of 1-bromo-2-vinylbenzene derivatives with internal alkynes was realized for the efficient synthesis of substituted naphthalenes. A controllable aryl to vinylic 1,4-palladium migration process is the key for success.

An atom- and pot-economical consecutive multi-step reaction approach to polycyclic aromatic hydrocarbons (PAHs)

A novel one-pot benzannulation reaction has been developed for the synthesis of substituted polycyclic aromatic hydrocarbons (PAHs) from the direct coupling of propargylic aldehydes/alcohols with 1,1-diarylethanol through an atom-economical uninterrupted three/four-step reaction sequence under mild and metal-free reaction conditions. The strategy involves an acid-catalyzed dehydration and carbon-carbon bond formation followed by DBU-promoted cycloisomerization. Naphthalene and phenanthrene were obtained via mono-benzannulation, and chrysene, picene and benzopicene were obtained involving consecutive di-benzannulation reactions in good yields starting from easily accessible starting materials.

Iron-catalysed tandem cross-dehydrogenative coupling (CDC) of terminal allylic C(sp3) to C(sp2) of styrene and benzoannulation in the synthesis of polysubstituted naphthalenes

A novel iron-catalysed tandem cross-dehydrogenative coupling and benzoannulation process was developed for the synthesis of biologically and synthetically important polysubstituted naphthalene derivatives from simple 1,2-aryl-propenes and styrenes in moderate to good yields. The Royal Society of Chemistry 2012.