60253-25-0

Upstream product

• 942264-65-5 1-bromo-2-(2-(4-fluorophenyl)-2-phenylethyl)benzene 
• 573-17-1 9-bromophenanthrene 
• 1765-93-1 4-fluoroboronic acid 
• 1994-55-4 9-(4-fluorophenyl)-9-chlorofluorene 
• 85-01-8 phenanthrene 
• 17236-60-1 trichloro-(4-fluorophenyl)stannane 
• 455-17-4 (p-fluorophenyl)trimethylsilane 
• 352-13-6 4-flourophenylmagnesium bromide 
• 615-36-1 2-bromoaniline 
• 98-80-6 phenylboronic acid 
• 766-98-3 1-ethynyl-4-fluorobenzene 
• 318-13-8 [1,1'-biphenyl]-2-diazonium tetrafluoroborate 
• 90-41-5 2-phenylaniline 
• 108-86-1 bromobenzene 

Relevant academic research and scientific papers

Preparation method of fused ring compound

The invention discloses a preparation method of a fused ring compound III. The preparation method comprises the following step: in a solvent and in the presence of palladium acetate, alkali and a ligand, carrying out a reaction shown in the specification on a compound I and a compound II to obtain a compound III. The preparation method disclosed by the invention is relatively good in compatibilitywith a substrate, various polycyclic aromatic hydrocarbon compounds can be simply obtained in a short period of time through convergent synthesis, and particularly, heteroatom-containing polycyclic aromatic hydrocarbon shows extremely excellent regioselectivity.

Br?nsted Acid-Catalyzed Carbocyclization of 2-Alkynyl Biaryls

Ortho-alkynyl biaryls react in the presence of catalytic amount of Br?nsted acids to give phenanthrenes in high yields under mild conditions. The activity and selectivity of this transformation are governed by the substitution pattern of the diarylalkyne moiety. Selectivity shifts are observed between the carbophilic Lewis and Br?nsted acid-catalyzed cycloisomerization involving alkyne activation. (Figure presented.).

Orthogonal Nanoparticle Catalysis with Organogermanes

Although nanoparticles are widely used as catalysts, little is known about their potential ability to trigger privileged transformations as compared to homogeneous molecular or bulk heterogeneous catalysts. We herein demonstrate (and rationalize) that nanoparticles display orthogonal reactivity to molecular catalysts in the cross-coupling of aryl halides with aryl germanes. While the aryl germanes are unreactive in LnPd0/LnPdII catalysis and allow selective functionalization of established coupling partners in their presence, they display superior reactivity under Pd nanoparticle conditions, outcompeting established coupling partners (such as ArBPin and ArBMIDA) and allowing air-tolerant, base-free, and orthogonal access to valuable and challenging biaryl motifs. As opposed to the notoriously unstable polyfluoroaryl- and 2-pyridylboronic acids, the corresponding germanes are highly stable and readily coupled. Our mechanistic and computational studies provide unambiguous support of nanoparticle catalysis and suggest that owing to the electron richness of aryl germanes, they preferentially react by electrophilic aromatic substitution, and in turn are preferentially activated by the more electrophilic nanoparticles.

Sequential Cross-Coupling/Annulation of ortho-Vinyl Bromobenzenes with Aromatic Bromides for the Synthesis of Polycyclic Aromatic Compounds

A sequential cross-coupling/annulation of ortho-vinyl bromobenzenes with aromatic bromides was realized, providing a direct and modular approach to access polycyclic aromatic compounds. A vinyl-coordinated palladacycle was proposed as the key intermediate for this sequential process. Excellent chemoselectivity and regioselectivity were observed in this transformation. The practicability of this method is highlighted by its broad substrate scope, excellent functional group tolerance, and rich transformations associated with the obtained products.

Metal-free cycloisomerizations of: O -alkynylbiaryls

We describe a novel and highly efficient metal-free strategy to construct 9,9-disubstituted fluorenes and phenanthrenes via the TfOH-catalyzed cycloisomerizations of o-alkynylbiaryls. Notably, the significant effects of the electronic properties and steric hindrance of the alkyne terminus on the reaction selectivity have been observed.

A new route to π-extended polycyclic aromatic hydrocarbons via cross-dehydrogenative coupling

A palladium-catalyzed cross-dehydrogenative coupling of phenanthrenes with simple arenes was developed. This protocol provides an opportunity for producing π-extended polycyclic aromatic hydrocarbons with minimum waste and high atomic efficiency under mild and ligand-free conditions.

Extended Study of Visible-Light-Induced Photocatalytic [4 + 2] Benzannulation: Synthesis of Polycyclic (Hetero)Aromatics

Herein we report an extended study of [4 + 2] benzannulation reactions of 2-(hetero)aryl-substituted anilines with alkynes by visible light photocatalysis. The method requires the use of tBuONO as a diazotizing agent and 0.3 mol % of fac-Ir(ppy)3 as a photocatalyst at room temperature. The reaction proceeded in a chemo- and regioselective manner with high functional group tolerance under mild conditions allowing the preparation of a wide variety of polycyclic (hetero)aromatic compounds, including phenanthrenes, in moderate to high yields. This procedure is amenable to gram-scale synthesis of 9-phenylphenanthrene.

Synthesis of Functionalized Phenanthrenes via Regioselective Oxidative Radical Cyclization

The majority of Sn-mediated cyclizations are reductive and, thus, cannot give a fully conjugated product. This is a limitation in the application of Sn-mediated radical cascades for the preparation of fully conjugated molecules. In this work, we report an oxidatively terminated Bu3Sn-mediated cyclization of an alkyne where AIBN, the commonly used initiator, takes on a new function as an oxidative agent. Sn-mediated radical transformation of biphenyl aryl acetylenes into functionalized phenanthrenyl stannanes can be initiated via two potentially equilibrating vinyl radicals, one of which can be trapped by the fast 6-endoclosure at the biphenyl moiety in good to excellent yields. The efficient preparation of Sn-substituted phenanthrenes opens access to convenient building blocks for the construction of larger polyaromatics.

N-heterocyclic-carbene complexes readily prepared from Di-μ-hydroxopalladacycles catalyze the Suzuki arylation of 9-bromophenanthrene

New cyclometalated palladium complexes of general formula [Pd(Bmim)(X)(C^N)] have been synthesized by a novel reaction route involving di-μ-hydroxo-palladacycles [{Pd(μ-OH)(C^N)}2] (C^N = 2-benzoylpyridine (Bzpy

KOt-Bu/DMF promoted intramolecular cyclization of 1,1′-biphenyl aldehydes and ketones: An efficient synthesis of phenanthrenes

A new synthesis of phenanthrene derivatives has been achieved through intramolecular cyclization of 1,1′-biphenyl aldehydes and ketones promoted by KOt-Bu/DMF. A free radical reaction pathway is proposed.