117408-90-9

Usage

InChI:InChI=1/C16H13I/c17-15-11-10-12-6-4-5-9-14(12)16(15)13-7-2-1-3-8-13/h1-9H,10-11H2

Upstream product

• 123994-49-0 3,4-dihydro-1-naphthyl triflate 
• 1078-58-6 diphenylzinc 
• 71-43-2 benzene 
• 2051-95-8 succinylbenzene 
• 1821-12-1 4-Phenylbutyric acid 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 7469-40-1 1-phenyl-3,4-dihydronaphthalene 
• 94051-93-1 1-phenyl-1,2,3,4-tetrahydronaphthalen-1-ol 
• 40164-53-2 1,4-diphenyl-1-butyne 

Downstream Products

• 206-44-0 fluoranthene 
• 607731-70-4 2-iodo-1-phenylnaphthalene 

Relevant academic research and scientific papers

Three-Component Difunctionalization of Cyclohexenyl Triflates: Direct Access to Versatile Cyclohexenes via Cyclohexynes

Difunctionalization of strained cyclic alkynes presents a powerful strategy to build richly functionalized cyclic alkenes in an expedient fashion. Herein we disclose an efficient and flexible approach to achieve carbohalogenation, dicarbofunctionalization, aminohalogenation and aminocarbonation of readily available cyclohexenyl triflates. We have demonstrated the novel use of zincate base/nucleophile system for effective formation of key cyclohexyne intermediates and selective addition of various carbon and nitrogen nucleophiles. Importantly, leveraging the resulting organozincates enables the incorporation of a broad range of electrophilic partners to deliver structurally diverse cyclohexene motifs. The importance and utility of this method is also exemplified by the modularity of this approach and the ease in which even highly complex polycyclic scaffolds can be accessed in one step.

Synthesis of uniformly 13C-labeled polycyclic aromatic hydrocarbons

Convergent synthetic pathways were devised for efficient synthesis of a series of uniformly 13C labeled polycyclic aromatic hydrocarbons de novo from U-13C-benzene and other simple commercially-available 13C-starting compounds. All target products were obtained in excellent yields, including the alternant PAH U-13C-naphthalene, U-13C-phenanthrene, U-13C-anthracene, U- 13C-benz[a]anthracene, U-13C-pyrene and the nonalternant PAH U-13C-fluoranthene.

Synthesis of naphthalenes and 2-naphthols by the electrophilic cyclization of alkynes

A wide variety of substituted naphthalenes are readily prepared regioselectively under mild reaction conditions by the 6-endo-dig electrophilic cyclization of appropriate arene-containing propargylic alcohols by IC1, I 2, Br2, NBS, and PhSeBr. 3-Iodo-2-naphthols have also been prepared in excellent yields by the cyclization of analogous 1-aryl-3-alkyn-2-ones. This methodology readily accommodates various functional groups and has been successfully extended to the synthesis of substituted carbazoles and dibenzothiophenes.

Intramolecular iodoarylation reaction of alkynes: Easy access to derivatives of benzofused heterocycles

The iodoarylation reaction of heteroatom-tethered ω-aryl-alkynes offers an efficient and straightforward entry to heterocycles. As a result, both C-C ring-closing from readily available precursors, and concomitant selective iodination take place. The firs