21015-56-5

Upstream product

• 912-17-4 1,2-diphenyl-1,2-bis-(4-chlorophenyl)-ethanediol 
• 115388-37-9 2,3-bis-(4-chloro-phenyl)-2,3-diphenyl-oxirane 
• 861004-92-4 10,10-bis-(4-chloro-phenyl)-9,10-dihydro-[9]phenanthrol 
• 7553-56-2 iodine 
• 64-19-7 acetic acid 
• 873-73-4 4-n-chlorophenylacetylene 
• 78704-49-1 1-(4-chlorophenyl)-2-trimethylsilylacetylene 
• 637-87-6 1-Chloro-4-iodobenzene 
• 591-50-4 iodobenzene 
• 1820-42-4 bis(4-chlorophenyl)acetylene 
• 88-65-3 2-bromobenzoic-acid 
• 15810-15-8 9,10‐dibromophenanthrene 
• 1679-18-1 4-Chlorophenylboronic acid 
• 13688-68-1 9,9-dimethyl-9-silafluorene 

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.

Organic electroluminescence material containing phenanthrene structure and organic luminescence device thereof

The invention provides an organic electroluminescence material containing a phenanthrene structure and an organic luminescence device thereof, and belongs to the technical field of organic photoelectric materials. The structure of the organic electroluminescence material containing the phenanthrene structure contains the phenanthrene ring structure, wherein the phenanthrene ring structure is a blue ray structure which is excellent in performance and has a higher triplet state energy level and a wider energy gap, and in molecules, through connection with benzimidazole groups, the electron transportation capability of the blue ray main structure is enhanced, so that carrier transportation is balanced. Compared with the prior art, the material has the advantages that the material is applied to the organic luminescence device and especially used as the blue luminescence material in a luminescence layer, the luminescence efficiency is relatively high, and the driving voltage is relatively low.

One-Step Annulative π-Extension of Alkynes with Dibenzosiloles or Dibenzogermoles by Palladium/o-chloranil Catalysis

Reliable and short synthetic routes to polycyclic aromatic hydrocarbons and nanographenes are important in materials science. Herein, we report an efficient one-step annulative π-extension reaction of alkynes that provides access to diarylphenanthrenes and related nanographene precursors. In the presence of a cationic palladium/o-chloranil catalyst system and dibenzosiloles or dibenzogermoles as π-extending agents, a variety of diarylacetylenes are transformed successfully into 9,10-diarylphenanthrenes in a single step with good functional-group tolerance. Furthermore, double π-extension reactions of 1,4-bis(phenylethynyl)benzene and diphenyl-1,3-butadiyne are demonstrated, affording oligoarylene products, which show potential for application in the synthesis of larger polycyclic aromatic hydrocarbons and nanographenes.

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.

Palladium-catalyzed intermolecular decarboxylative coupling of 2-phenylbenzoic acids with alkynes via C-H and C-C bond activation

A novel protocol for palladium-catalyzed intermolecular formal [4 + 2] annulation of 2-phenylbenzoic acids with alkynes is described. Acridine is shown to be essential for the high reaction efficiency. Phenanthrene derivatives are formed in moderate to good yields without coupling (pseudo)halides or organometallic species.

Preparation of Condensed Aromatics by Superacidic Dehydrative Cyclization of Arvl Pinacols and Eooxides

Aryl pinacols and epoxides, respectively, are cleanly and in high yield converted via superacidic dehydrative cyclization to the corresponding condensed aromatics. Dehydrative cyclization of benzopinacol (1a), triphenylacetophenone (2), and tetraphenylethylene oxide (9) give 9,10-diphenylphenanthrene (3a) as the major product in acidic media stronger than Ho = -11. Aryl pinacol 12a forms the condensed aromatic 13a as the major product in acidic media stronger than Ho = -13.5. It is proposed that the dehydrative cyclizations to provide aromatics 3a and 13a occurs through dicationic intermediates. Substituted benzopinacols 1f, 1g, and 1j are prepared and give the corresponding phenanthrenes (3f, 3g, and 3j) in high yields. The regiochemistry of the cyclization of substituted benzopinacols is controlled by deactivating substituents on the aryl rings. Aryl pinacols (12a-d) derived from acenaphthenequinone and pinacol 15 also give condensed aromatics (13a-d and 16, repectively) with superacidic triflic acid.

The preparation of substituted phenanthrenes from aryl pinacols in superacid

Reactions of aryl pinacols with the superacidic triflic acid give rise to substituted phenanthrenes in good yields.

Does diatomic sulfur (S2) react as a free species?

A detailed study into the design and synthesis of stable 1,2-dithietane derivatives for the generation of diatomic sulfur (S2) was undertaken. Computer-aided evaluation of enthalpic differences was used to direct the synthesis of target compounds and, although all of the compounds calculated to afford S2 that were prepared did yield diatomic sulfur, an isolable 1,2-dithietane other than dithiatopazine failed to materialize. The results of this study provide convincing evidence that the computational procedure outlined can be successfully used to predict the course of S2 extrusion pathways from potential dithionocarbonylated derivatives. To determine if the disulfide moiety found in the Diels-Alder adduct derived from the addition of diatomic sulfur to conjugated 1,3-dienes is due to a transference mechanism involving the transient 1,2-dithietane intermediate, a chiral nonracemic binaphthyl source of S2 was prepared. Reactions of S2 from this source with chiral nonracemic and prochiral conjugated 1,3-dienes indicate that the added disulfide moiety would be inconsistent with a transference mechanism and that a "free" acting S2 unit is more likely to be involved.