16939-14-3

Upstream product

• 53172-84-2 (E/Z)-2-phenylpent-2-ene 
• 29421-92-9 4-bromo-2-methylthiophene 
• 554-14-3 2-Methylthiophene 
• 98-80-6 phenylboronic acid 
• 96-43-5 2-thienyl chloride 
• 768-32-1 trimethylphenylsilane 
• 82323-38-4 (Z)-5-bromo-4-phenylpent-3-en-2-one 
• 591-50-4 iodobenzene 
• 98-09-9 benzenesulfonyl chloride 

Relevant academic research and scientific papers

Tris-NHC-propagated self-supported polymer-based Pd catalysts for heterogeneous C-H functionalization

Three-dimensionally propagated imidazolium-containing mesoporous coordination polymer and organic polymer-based platforms were successfully exploited to develop single-site heterogenized Pd-NHC catalysts for oxidative arene/heteroarene C-H functionalization reactions. The catalysts were efficient in directed arene halogenation, and nondirected arene and heteroarene arylation reactions. High catalytic activity, excellent heterogeneity and recyclability were offered by these systems making them promising candidates in the area of heterogeneous C-H functionalization, where efficient catalysts are still scarce.

Direct Arylations of Heteroarenes with Benzenesulfonyl Chlorides Using Pd/C Catalyst

The reactivity of heteroaromatics in direct arylation with benzenesulfonyl chlorides using 10 % Pd/C as catalyst was explored. With (benzo)thiophenes, (benzo)furans, pyrroles and selenophenes, high yields in arylated heteroarenes were obtained. These arylations were performed using only 5 mol-% Pd/C and Li2CO3 as inexpensive base. The regioselectivities are similar to those observed with homogeneous palladium catalysts. Better yields were obtained with electron-deficient benzenesulfonyl chlorides than with the electron-rich ones. Notably, useful substituents such as bromo or iodo on the benzenesulfonyl chloride were tolerated, as no cleavage of the C–Br or C–I bonds was observed under these conditions. The use of Pd/C presents several advantages compared to the previously employed homogeneous palladium catalysts, as it can be easily removed by filtration at the end of the reaction. The major side-products of the reaction are HBr associated to Li2CO3. Therefore, this new protocol affords a very attractive synthetic scheme in terms of cost, simplicity and low environmental impact for the access to arylated heteroaromatics.

Palladium-catalyzed dehydrogenative coupling of cyclic enones with thiophenes: A rapid access to β-heteroarylated cyclic enones

Dehydrogenative coupling of cyclic enones with heteroarenes has been a longstanding challenge because of the competitive ketone dehydrogenation and conjugated addition. Herein, a dehydrogenative coupling reaction of cyclic enones of different sizes with substituted thiophenes to construct β-thienyl cyclic enone compounds through palladium-catalyzed C-H functionalization under mild reaction conditions is reported. Simple substituted thiophenes with different functional groups can be directly introduced into cyclic enones with predominant regioselectivity at the α position of thiophene moieties and excellent functional group tolerance. Further molecular transformations of the coupling products to synthetically useful meta-heteroarylated phenol derivatives have also been demonstrated.

Selective β-Arylation of Thiophenes with Aryl Iodides Catalyzed by Dinuclear Palladium Carboxylate Complexes

Novel dinuclear palladium complexes bearing acetoxy ligands were synthesized and characterized by X-ray crystal analysis. The complexes were utilized for the arylation of 2-ethylthiophene with iodobenzene to give ethylphenylthiophenes with high β selectiv

γ-halo-enones: A method for their synthesis from arylacyl halides and their application to the preparation of five-membered ring heterocycles

A simple method has been developed for synthesis of γ-halo-enones. The approach employs a sequence involving initial indium-mediated allenylation reactions of phenacyl halides with propargyl bromide. This process is followed by acid-promoted rearrangement reactions of the formed homoallenic halohydrins. The new method can be incorporated into routes for the efficient synthesis of various five-membered heterocyclic compounds.

Benzenesulfonyl chlorides: New reagents for access to alternative regioisomers in palladium-catalysed direct arylations of thiophenes

The palladium-catalysed coupling of benzenesulfonyl chlorides with thiophene derivatives allows regioselective access to β-arylated thiophenes. The reaction proceeds with easily accessible catalyst, base and substrates, without oxidant or ligand and tolerates a variety of substituents on both the benzene and thiophene moieties.

Pd-catalyzed β-selective direct C-H bond arylation of thiophenes with aryltrimethylsilanes

Direct arylation of thiophenes and benzothiophenes with aryltrimethylsilanes was effectively catalyzed by PdCl2(MeCN) 2 in the presence of CuCl2 as an oxidant. The reaction preferentially occurred at the β-position of both

Oxidative biaryl coupling of thiophenes and thiazoles with arylboronic acids through palladium catalysis: Otherwise difficult C4-selective C-H arylation enabled by boronic acids

(Chemical Equation Presented) It adds up to 4! Thiophenes and thiazoles can be arylated in the 4- rather than the expected 5-position in a new C-H functionalization reaction (see scheme; TEMPO: 2,2,6,6-tetramethylpiperidine-N- oxyl). The boronic acid proved to be the key to achieving the otherwise difficult C4 selectivity. The method was applied to a concise synthesis of a key pharmacological structure with potential for treatment of Alzheimers disease.

Efficient method for the synthesis of hetarenoindanones based on 3-arylhetarenes and their conversion into hetarenoindenes

A series of hetarenoindanones have been prepared by direct double metalation of the appropriate 3-phenylhetarene with butyllithium in the presence of TMEDA followed by treatment of the resulting dilithium compound with ethyl N ,N-dimethylcarbamate. All hetarenoindanones were reduced according to Wolff-Kishner by hydrazine in the presence of KOH to the corresponding hetarenoindenes.