68695-87-4

Upstream product

• 116027-68-0 9,10-di(p-tolyl)-9,10-dihydro-phenanthrene-9,10-diol 
• 259-79-0 bisbenzocyclobutene 
• 2789-88-0 1,2-bis(4-methylphenyl)acetylene 
• 14002-52-9 o-phenylbenzoyl chloride 
• 947-84-2 2-Biphenylcarboxylic acid 
• 189999-35-7 [1,1'-biphenyl]-2,2'-iodonium trifluoromethanesulfonate 
• 624-31-7 4-tolyl iodide 
• 31274-15-4 7,8-Benzobicyclo[4.2.0]okt-7-en-1-ol 
• 2052-07-5 2-Bromobiphenyl 
• 591-50-4 iodobenzene 
• 88-65-3 2-bromobenzoic-acid 
• 583-55-1 1-Bromo-2-iodobenzene 
• 98-80-6 phenylboronic acid 
• 85-44-9 phthalic anhydride 

Downstream Products

• 1010812-15-3 9,10-di(4-bromomethylphenyl)-phenanthrene 

Relevant academic research and scientific papers

Synthesis of Phenanthrenes via Palladium-Catalyzed Three-Component Domino Reaction of Aryl Iodides, Internal Alkynes, and o-Bromobenzoic Acids

A new palladium-catalyzed domino alkyne insertion/C-H activation/decarboxylation sequence has been developed, which provides an efficient approach for synthesizing a variety of functionalized phenanthrenes in moderate to good yields. The method shows broad substrate scope and good functional group tolerance by employing readily available materials, including aryl iodides, internal alkynes, and o-bromobenzoic acids, as three-component coupling partners.

A palladium-catalyzed multi-component annulation approach towards the synthesis of phenanthrenes

An efficient palladium-catalyzed three-component cascade reaction has been developed for the facile construction of phenanthrene frameworks. The transformation is driven by a controlled reaction sequence of Suzuki-Miyaura coupling followed by the insertion of alkynes, and finally, annulation to yield phenanthrene derivatives via C-H activation. This methodology is able to accommodate a variety of substrates and affords the anticipated products in good to excellent yields.

π-CONJUGATED COMPOUND AND METHOD FOR PRODUCING THE SAME

PROBLEM TO BE SOLVED: To provide π-conjugated compounds having various skeletons and a simple method for synthesizing the same and to provide a new π-conjugated compound. SOLUTION: There is provided a method for producing a π-conjugated compound which comprises a step of reacting a compound A and a compound B in the presence of an aprotic solvent, followed by subjecting the resulting borepin derivative to oxidation reaction. The compound A contains at least one of alkynyl groups directly bonded to a carbon atom and the compound B contains a unit in which a halogen atom (provided that a fluorine atom is excluded) or a trifluoromethanesulfonyl group and two aryl groups which may be bonded to each other to form a ring are directly bonded to boron. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT

Phenanthrene Synthesis via Chromium-Catalyzed Annulation of 2-Biaryl Grignard Reagents and Alkynes

A chromium/2,2′-bipyridine-catalyzed annulation reaction of 2-biarylmagnesium reagents with alkynes is reported. The reaction is applicable to a variety of aryl- and/or alkyl-substituted internal alkynes as well as 2-biaryl and related Grignard reagents, thus affording phenanthrene derivatives in moderate to good yields. The reaction proceeds at the expense of excess alkyne as a hydrogen acceptor and thus does not need an external oxidant. Deuterium-labeling experiments shed light on the reaction mechanism, which likely involves multiple intramolecular C-H activation processes on chromium.

Synthesis of multiply substituted polycyclic aromatic hydrocarbons by iridium-catalyzed annulation of ring-fused benzocyclobutenol with alkyne through C-C bond cleavage

The first iridium-catalyzed intermolecular cyclization between alkynes and ring-fused benzocyclobutenols (RBCB) through C-C bond cleavage is described. A variety of elusive polycyclic aromatic hydrocarbons (PAHs) with multiple substituents are obtained in good yields under mild conditions. This procedure provides a unique and expeditious tool for the synthesis of PAHs. Expanding the family: The iridium-catalyzed intermolecular cyclization between ring-fused benzocyclobutenols and alkynes through C-C bond cleavage is described. A variety of elusive polycyclic aromatic hydrocarbons (PAHs) with multiple substituents are obtained in good yields under mild conditions. The transformation exhibits good functional-group tolerance and regioselectivity.

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.

Three-bond breaking of cyclic anhydrides: Easy access to polyfunctionalized naphthalenes and phenanthrenes

Benzannulation of phthalic anhydrides with alkynes to polyfunctionalized naphthalenes and phenanthrenes was confirmed to be straightforward using a palladium catalytic system. Sequential liberation of CO2 and CO occurred via oxidative decomposition of anhydride. In the case of 1,8-naphthalenedicarboxylic anhydrides, both aryls were encompassed in the annulation reaction to afford acenaphthylenes.

Synthesis of diarylated aromatic hydrocarbons by dehydroxylation of diols using the titanium(IV) chloride and triethylamine reagent system

1,2-Diarylacenaphthylene, 9,10-diarylphenanthrene and 9,10-diarylanthracene derivatives were obtained in good yields (61-92%) in short reaction times (5-30 min) from the corresponding diols with the titanium(III) reagent prepared in situ using the TiCl4/Et3N reagent system in dichloromethane at 25 °C. Georg Thieme Verlag Stuttgart ? New York.

Synthesis of aromatic compounds by catalytic C-C bond activation of biphenylene or angular [3]phenylene

Substituted phenanthrenes and picenes were easily prepared by reaction of biphenylene or angular [3]phenylene with various alkynes in the presence of a catalytic amount of [IrCl(cod)]2/dppe (cod=1,5-cyclooctadiene, dppe=1,2-bis(diphenylphosphin