60300-72-3

Upstream product

• 60300-79-0 (Z)-9-(1,2-diphenylvinyl)phenanthrene 
• 573-17-1 9-bromophenanthrene 
• 501-65-5 diphenyl acetylene 
• 2789-88-0 1,2-bis(4-methylphenyl)acetylene 
• 947-72-8 9-chlorophenanthrene 
• 10271-65-5 2-(phenylethynyl)-1,1'-biphenyl 
• 2113-51-1 2-iodobiphenyl 

Downstream Products

• 13579-05-0 phenanthro[9,10-e]acephenanthrylene 

Relevant academic research and scientific papers

Palladium-Catalyzed Dimerization of Bis(2-biphenylyl)acetylene toward Sterically Hindered Acephenanthrylene

The reaction of 2,2′′-(1,2-ethynediyl)bis-1,1′-biphenyl under homogeneous (heterogeneous) catalysis with Pd/C/TMS-Cl results in a dimerization and the additional formation of five- and six-membered rings. The steric demand of the acetylene prevents a [2 + 2 + 2] cycloaddition, but paves the way toward an alternative reaction. By the formation of an unexpected planar acephenanthrylene, the system avoids steric stain. The synthetic scope and requirements are explored, and a reaction mechanism is proposed.

Palladium-catalyzed annulation of 9-halophenanthrenes with alkynes: Synthesis, structural analysis, and properties of acephenanthrylene-based derivatives

The palladium-catalyzed annulation of 9-bromoand 9-chlorophenanthrenes with alkynes gave 4,5-disubstituted acephenanthrylenes in yields of 58-95% (9 examples). Asymmetric alkynes, such as 1-phenyl-1-propyne, 1-phenyl-1-hexyne, and 1-cyclopropyl-2-phenylethyne, regioselectively form (cyclo)alkyl-substituted products, following the regular rule that governs the carbopalladation of alkynes. This synthetic protocol can also be utilized in annulations with several p-extended bromoarenes, such as 7-bromo[5]helicene, 5-bromo[4]helicene, 9-bromoanthracene, 3-bromoperylene, and 3-bromofluoranthene, to give the corresponding annulated products in moderate to good yields (51-86%; 6 examples). Similarly, bromocorannulene produced highly curved 1,2-disubstituted cyclopentacorannulenes. Reactions of 6,12-dibromochrysene and 4,7-dibromo[4]helicene with di(4-tolyl) ethyne provided the twofold annulated products in moderate yields. 4,5-Diphenylacephenanthrylene and 6,7-diphenylbenzo[ a]acephenanthrylene thus generated were converted into phenanthro[9,10-e]acephenanthrylene and benzo[ a]phenanthro[9,10-e]acephenanthrylene, respectively, by oxidative cyclodehydrogenation. The structures of 4,5-diphenylacephenanthrylene, 4,5-diphenyldibenzo[a,l]acephenanthrylene, 1,2-diarylcyclopentacorannulenes, and benzo[ a]-phenanthro[9,10-e]acephenanthrylene were verified by X-ray crystallography. The photophysical and electrochemical properties of the selected annulated products were investigated.