33498-62-3

Usage

InChI:InChI=1/C21H16/c1-15-17-11-5-6-12-18(17)19-13-7-8-14-20(19)21(15)16-9-3-2-4-10-16/h2-14H,1H3

Upstream product

• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 4433-15-2 2-biphenyl-2-yl-3,3-dimethyl-2-phenyl-oxirane 
• 10035-10-6 hydrogen bromide 
• 64-19-7 acetic acid 
• 23533-35-9 biphenyl-2-ylmagnesium iodide 
• 6630-91-7 9-methyl-10-methylene-9-phenyl-9,10-dihydro-phenanthrene 
• 673-32-5 1-Phenylprop-1-yne 
• 591-50-4 iodobenzene 
• 88-65-3 2-bromobenzoic-acid 
• 108-86-1 bromobenzene 
• 583-55-1 1-Bromo-2-iodobenzene 
• 98-80-6 phenylboronic acid 
• 197251-03-9 (Z)-2,2'-(1-phenylprop-1-ene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) 

Downstream Products

• 86853-96-5 13H-indeno[1,2-l]phenanthren-13-one 
• 17024-30-5 10-phenyl-phenanthrene-9-carboxylic acid 

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.

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.

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.

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.

Base-catalyzed diborylation of alkynes: synthesis and applications of cis-1,2-bis(boryl)alkenes

An efficient, transition-metal free, and practical approach to cis-bis(boryl)alkenes from various alkynes was disclosed in the presence of a catalytic amount of K2CO3 under mild conditions. Meanwhile, tetrasubstituted alkenes and phenanthrene derivatives were readily constructed from the target diborylalkenes via Suzuki-Miyaura cross coupling.

Phenanthrene Synthesis by Palladium(II)-Catalyzed γ-C(sp2)-H Arylation, Cyclization, and Migration Tandem Reaction

Phenanthrene is an important structural motif in chemistry and materials science, and many synthetic routes have been developed to construct its skeleton. However, synthesis of unsymmetric phenanthrenes remains a challenge. Here, an efficient one-pot tandem reaction for the preparation of phenanthrenes via sequential γ-C(sp2)-H arylation, cationic cyclization, dehydration, and 1,2-migration was developed. A wide range of symmetric and unsymmetric phenanthrenes with diversified functional groups were synthesized with good to excellent yields.

Pd(II)-NHDC-Functionalized UiO-67 Type MOF for Catalyzing Heck Cross-Coupling and Intermolecular Benzyne-Benzyne-Alkene Insertion Reactions

A novel palladium N-heterocyclic bis-carbene dicarboxylate ligand (Pd-NHDC-H2L) was successfully synthesized. In addition, an Pd-NHDC-containing UiO-67 type MOF (UiO-67-Pd-NHDC) was prepared on the basis of a size-matched ligand mixture of biphenyl-4,4′-dicarboxylic acid/Pd-NHDC-H2L (9/1) and ZrCl4 under solvothermal conditions. The obtained UiO-67-Pd-NHC MOF can be a highly heterogeneous catalyst to promote Heck cross-coupling and intermolecular benzyne-benzyne-alkene insertion reactions.

Phenanthrene Synthesis by Palladium-Catalyzed Benzannulation with o-Bromobenzyl Alcohols through Multiple Carbon-Carbon Bond Formations

A palladium-catalyzed benzannulation with o-bromobenzyl alcohols enabled the facile construction of phenanthrene skeletons via the sequential multiple carbon-carbon bond formations. A variety of multisubstituted phenanthrenes were synthesized by the reaction of (Z)-β-halostyrenes with o-bromobenzyl alcohols as well as by the three-component coupling of alkynes, aryl bromides, and o-bromobenzyl alcohols. The electron-deficient phosphine ligand played an important role to control the sequential oxidative addition of two different organic halides employed, which realized the selective formation of the desired phenanthrenes in good yields. This synthetic protocol was also applicable to the synthesis of the highly fused polycyclic aromatic hydrocarbons such as tetraphenes.

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.

Facile Synthesis of Polycyclic Aromatic Hydrocarbons: Br?nsted Acid Catalyzed Dehydrative Cycloaromatization of Carbonyl Compounds in 1,1,1,3,3,3-Hexafluoropropan-2-ol

The cycloaromatization of aromatic aldehydes and ketones was readily achieved by using a Br?nsted acid catalyst in 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP). In the presence of a catalytic amount of trifluoromethanesulfonic acid, biaryl-2-ylacetaldehydes and 2-benzylbenzaldehydes underwent sequential intramolecular cationic cyclization and dehydration to afford phenacenes and acenes, respectively. Furthermore, biaryl-2-ylacetaldehydes bearing a cyclopentene moiety at the α-position underwent unprecedented cycloaromatization including ring expansion to afford triphenylenes. HFIP effectively promoted the cyclizations by suppressing side reactions presumably as a result of stabilization of the cationic intermediates.