312612-69-4

Upstream product

• 14002-52-9 o-phenylbenzoyl chloride 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 
• 189999-35-7 [1,1'-biphenyl]-2,2'-iodonium trifluoromethanesulfonate 
• 13029-09-9 2,2'-dibromobiphenyl 
• 947-84-2 2-Biphenylcarboxylic acid 

Downstream Products

• 312612-61-6 9-iodo-10-phenylphenanthrene 

Relevant academic research and scientific papers

Pd catalyzed insertion of alkynes into cyclic diaryliodoniums: A direct access to multi-substituted phenanthrenes

Cyclic diaryliodoniums remain unexplored compared to linear iodoniums. In our current work, internal alkynes were for the first time applied to react with cyclic iodoniums, catalyzed by Pd, resulting in a [4 + 2] benzannulation. Our work offers a new strategy to synthesize multi-substituted phenanthrene derivatives which are not easily accessed by conventional methods.

Iridium-catalyzed annulative coupling of 2-arylbenzoyl chlorides with alkynes: Selective formation of phenanthrene derivatives

2-Arylbenzoyl chlorides undergo annulative coupling with internal alkynes in the presence of a catalyst system of [IrCl(cod)]2/P(t-Bu)3 to selectively afford the corresponding phenanthrene derivatives accompanied by elimination of carbon monoxide and hydrogen chloride. The reaction occurs without addition of any external base. Deuterium-labeling experiments using 2-(d5-phenyl)benzoyl chloride suggest that the rate-determining step does not involve the C2′-H bond cleavage. Formation of a [(t-Bu)3PH][(biphenyl-2,2′-diyl)Ir(CO)Cl2] complex dimer, of which the structure was determined by single-crystal X-ray analysis, from a stoichiometric reaction at 60 °C without addition of alkyne also supports the facile C-H cleavage.

Chromium-mediated synthesis of polycyclic aromatic compounds from halobiaryls

(Chemical Equation Presented) Reaction of 2,2′-dihalobiphenyl with butyllithium followed by the addition of chromium(III) chloride and alkynes afforded the corresponding phenanthrene derivatives via formal [4 + 2] cycloaddition. A variety of alkynes could be used for this reaction, such as alkyl, aryl, silyl, and alkoxycarbonyl alkynes. Repetitive process of the reaction gave more extended polycyclic compounds such as benzo[g]chrysene and azacyclopentaphenalene derivatives.