93564-13-7

Upstream product

• 504-24-5 4-aminopyridine 
• 108-67-8 1,3,5-trimethyl-benzene 
• 19524-06-2 4-bromopyridine hydrochloride 
• 2633-66-1 2-mesitylmagnesium bromide 
• 55-22-1 pyridine-4-carboxylic acid 
• 576-83-0 2,4,6-trimethylphenyl bromide 
• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 

Downstream Products

• 93564-18-2 N-<3-Mesityl-5-(2,4-cyclopentadienyliden)-1,3-pentadienyl>-N-methylanilin 
• 93564-17-1 3-Mesityl-5-(N-methylanilino)-2,4-pentadien-1-al 
• 93564-12-6 6-Mesitylazulen 
• 93564-14-8 <3-Mesityl-5-(N-methylanilino)-2,4-pentadienyliden>methylphenylammonium-bromid 

Relevant academic research and scientific papers

The use of organolithium reagents for the synthesis of 4-aryl-2-phenylpyridines and their corresponding iridium(III) complexes

A versatile palladium-free route for the synthesis of 4-aryl-substituted phenylpyridines (ppy), starting from tert-butyl 4-oxopiperidine-1-carboxylate, is reported. Reaction with an aryllithium, followed by trifluoroacetic acid dehydration/deprotection and oxidation with 2-iodoylbenzoic acid and finally phenylation, gave 4 ligands (L1-4H): 2,4-diphenylpyridine, 4-(4-methoxyphenyl)-2-phenylpyridine, 2-phenyl-4-(o-tolyl)pyridine and 4-mesityl-2-phenylpyridine. These ligands were coordinated to iridium to give the corresponding Ir(L)2(A) complexes (Ir1-7), where A = ancillary ligand acetylacetate or 2-picolinate. This was used to demonstrate that, through a combination of ancillary ligand choice and torsional twisting between the 4-aryl substituents of the ppy ligands, it is possible to tune the phosphorescent emission of the complexes in the range 502-560 nm.

Palladium dichloride adduct of N,N-bis-(diphenylphosphanylmethyl)-2- aminopyridine: Synthesis, structure and catalytic performance in the decarboxylative cross-coupling of 4-picolinic acid with aryl bromide

Reaction of PdCl2 with N,N-bis-(diphenylphosphanylmethyl)-2- aminopyridine (bdppmapy) afforded a mononuclear complex [(bdppmapy)PdCl 2] (1). Compound 1 was characterized by elemental analysis, IR, 1H, 13C and 31P NMR, electrospray ion mass spectra (ESI-MS) and X-ray single crystal crystallography. The Pd(ii) center in 1 is chelated by bdppmapy, showing a cis-square planar geometry. With the assistance of additive Cu2O, complex 1 exhibited good catalytic activity toward the decarboxylative cross-coupling reactions between 4-picolinic acid and aryl bromides. In the presence of only 2 mol% catalyst, a family of 4-aryl-pyridines could be isolated in up to 83% yield.

Syntheses of substituted pyridines, quinolines and diazines via palladium-catalyzed cross-coupling of aryl Grignard reagents

The palladium-catalyzed cross-coupling reactions between arylmagnesium halides (phenylmagnesium chloride, mesitylmagnesium bromide, 4-(methoxycarbonyl)phenylmagnesium chloride and 4-cyanophenylmagnesium chloride) and halopyridines allowed the synthesis of substituted pyridines. Owing to the remarkably mild conditions used (often below 0°C), the reaction could be extended to the use of functionalized halopyridines, haloquinolines and halodiazines.

Syntheses of Mesityl-substituted Azulenes

The five position isomer mesityl-substituted azulenes 1-5 have been prepared for the first time. 1- and 5-mesitylazulene (1 and 4) have been obtained by addition of mesityl-Li to appropriate ketonic precursors followed by dehydration and dehydrogenation w