150587-22-7

Upstream product

• 6831-91-0 5-methyl-1-phenylpyrazole 
• 591-50-4 iodobenzene 
• 822-36-6 4-methyl-1H-imidazole 
• 822-36-6 4-Methylimidazole 
• 108-86-1 bromobenzene 
• 639-58-7 triphenyltin chloride 
• 7164-98-9 1-phenylimidazole 
• 74-88-4 methyl iodide 

Relevant academic research and scientific papers

Triphenyltin chloride as a new source of phenyl group for C-heteroatom and C-C bond formation

Ph3SnCl is introduced as a very suitable source of phenyl group for coupling with phenols, amines, and thiols in the presence of Cu(OAc)2 in Et3N at room temperature to give aryl ethers, amines, and arylthio ethers in high yields. In addition, the application of Ph3SnCl in the Stille coupling of aryl halides in the presence of Pd(0) catalyst in PEG 400 at 110C is discussed.

α-d-Galacturonic Acid as Natural Ligand for Selective Copper-Catalyzed N-Arylation of N-Containing Heterocycles

The first application of α-d-galacturonic acid hydrate (GalA) is reported here, as a potential O-donor ligand. The C-N couplings of N-heterocycles with aryl halides or arylboronic acids could be readily conducted and exhibited good functional group tolerance with characters of selectivity. These N-Arylazoles allow rapid access to several pharmaceutical intermediates and can be easily transformed into a variety of other interesting scaffolds as well.

Copper(I)-USY as a Ligand-Free and Recyclable Catalyst for Ullmann-Type O-, N-, S-, and C-Arylation Reactions: Scope and Application to Total Synthesis

The copper(I)-doped zeolite CuI-USY proved to be a versatile, efficient, and recyclable catalyst for various Ullmann-type coupling reactions. Easy to prepare and cheap, this catalytic material enables the arylation and heteroarylation of diverse O-, N-, S-, and C-nucleophiles under ligand-free conditions while exhibiting large functional group compatibility. The facility of this catalyst to promote C-O bond formation was further demonstrated with the total synthesis of 3-methylobovatol, a naturally occurring diaryl ether of biological relevance. From a mechanistic viewpoint, two competitive pathways depending on the nature of the nucleophile and consistent with the obtained results have been proposed.

Facile cuI-catalyzed arylation of azoles and amides using simple enaminones as efficient ligands

(E)-3-(Dimethylamino)-1-(2-hydroxyphenyl)prop-2-en-1-one was found to be an excellent ligand for copper-catalyzed N-arylation of azoles and amides with aryl halides under mild conditions. The reaction took place at 82 C in MeCN with broad functional-group compatibility. A combination of the ligand and CuI proved to be an efficient catalytic system to promote the coupling reactions of aryl halides with azoles and amides.

Cadmium(II)-catalyzed C-N cross-coupling of amines with aryl iodides

Cadmium diacetate dihydrate [Cd(OAc)2·2H2O] in combination with ethylene glycol catalyzes efficiently the C-N cross-coupling of amines with aryl iodides by a benzyne mechanism. Alkyl, aryl and heterocyclic amines are compatible with this system affording the aminated products in high to excellent yield.

Simple copper salt-catalyzed N-arylation of nitrogen-containing heterocycles with aryl and heteroaryl halides

(Chemical Equation Presented) Relatively mild and highly efficient CuI-catalyzed N-arylation procedures for nitrogen-containing heterocycles (e.g., imidazoles, benzimidazoles, pyrroles, pyrazoles, indoles, triazoles, etc.) with aryl and heteroaryl halides have been developed. The protocols can be performed easily and tolerate a number of functional groups, such as ester, nitrile, nitro, ketone, free hydroxyl, and free primary amine on the aryl halide.

Novel CuO nanoparticle catalyzed C - N cross coupling of amines with Lodobenzene

CuO nanoparticles catalyze the C-N cross coupling of amines with iodobenzene in excellent yields. The reaction is simple and efficient and operates under air with ligand free conditions. The catalyst is recyclable without loss of activity.

An efficient copper-catalyzed coupling of aryl halides with imidazoles

Copper-catalyzed N-arylation of imidazoles can be accomplished using (CuOTf)2 · benzene as a copper source and Cs2CO3 as a base in xylenes at 110-125 °C. Addition of 1,10-phenanthroline (phen) and trans, trans- dibenzylide

Phototransposition chemistry of 1-Phenylpyrazole. Experimental and computational studies

Photophysical and photochemical properties of 1-phenylpyrazole and 3-,4-, and 5-methyl-1-phenylpyrazoles have been investigated. INDO/S calculations agree with experimental measurements which show that the S1 and T1 states of these c