22145-08-0

Upstream product

• 16939-57-4 (E)-buta-1,3-dienylbenzene 
• 696-62-8 para-iodoanisole 
• 538-51-2 benzylidene phenylamine 
• 4180-23-8 E-1-(4'-methoxyphenyl)prop-1-ene 
• 140653-96-9 (4-Methoxy-phenyl)-(2-phenyl-cyclopropyl)-methanol 
• 24680-50-0 4-methoxy-trans-cinnamaldehyde 
• 100-44-7 benzyl chloride 
• 637-69-4 4-Methoxystyrene 
• 588-72-7 [(E)-2-bromoethenyl]benzene 
• 853335-26-9 2-((1E,3E)-4-(4-methoxyphenyl)buta-1,3-dienyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 17763-67-6 Phenyl triflate 
• 103-64-0 bromostyrene 
• 1963-36-6 4-methoxycinnamaldehyde 
• 1449-46-3 benzyltriphenylphosphonium bromide 

Downstream Products

• 1170321-07-9 1-(4-methoxyphenyl)-4-phenylnaphthalene 
• 1206103-27-6 (1E,3E)-1-(4-hydroxyphenyl)-4-phenyl-1,3-butadiene 
• 82102-30-5 cis-2-(p-methoxyphenyl)-5-phenyl-8-oxabicyclo<4.3.0>non-3-ene-7,9-dione 
• 16939-57-4 (E)-buta-1,3-dienylbenzene 
• 14371-10-9 (E)-3-phenylpropenal 
• 24680-50-0 4-methoxy-trans-cinnamaldehyde 
• 100-52-7 benzaldehyde 
• 59086-11-2 2-(4-methoxyphenyl)-5-phenylthiophene 
• 150660-28-9 (E)-1-methoxy-4-(4-phenylbut-1-en-1-yl)benzene 
• 22263-99-6 2-Phenyl-5-(p-methoxy-phenyl)-pentadien-(2cis,4trans)-al-⁽¹⁾ 
• 37985-01-6 (E)-1-methoxy-4-(4-phenylbut-2-en-1-yl)benzene 

Relevant academic research and scientific papers

Regio- and Stereoselective Diarylation of 1,3-Dienes via Ni/Cr Cocatalysis

Through the formation of the thermodynamically favored Cr(III)-O bond, the Nozaki-Hiyama-Kishi reaction has been widely applied in the functionalization of carbonyl compounds with the help of Ni catalysis. Herein, a divergent regio- and stereoselective diarylation of dienes has been developed under Ni/Cr cocatalysis without the inherent driving force for the formation of polar metal alkoxides. Preliminary experimental studies have been conducted to elucidate the key roles of Ni, Cr, and redox-active bis(imino)pyridine (PDI) ligands. The proposed mechanism suggests that the newly formed C-C bond of this diarylation was created by organonickel species instead of organochromium species.

Pd-Catalyzed Cross-Coupling of Organostibines with Styrenes to Give Unsymmetric (E)-Stilbenes and (1 E,3 E)-1,4-Diarylbuta-1,3-dienes and Fluorescence Properties of the Products

A general and effective palladium-catalyzed cross-coupling of organostibines with styrenes to give (E)-olefins was disclosed. By the use of an organostibine reagent, this method can produce unsymmetric (E)-1,2-diarylethylenes and (1E,3E)-1,4-diarylbuta-1,3-dienes in good yields with high E/Z selectivity and good functional group tolerance. Resveratrol and DMU-212 were synthesized in high yield. The protocol can be extended to the synthesis of (1E,3E,5E)-1,6-diphenylhexa-1,3,5-triene in 40% yield. Products 5e, 5f, and 7a showed good photoluminescence quantum yields ranging from 72 to 99%.

Iron(III)/O2-Mediated Regioselective Oxidative Cleavage of 1-Arylbutadienes to Cinnamaldehydes

A simple, efficient, and environmentally benevolent regioselective oxidative cleavage of 1-arylbutadienes to cinnamaldehydes mediated by iron(III) sulfate/O2 has been developed. The reaction offered good yields and excellent regioselectivity and showed good functional group tolerance (31 examples). The method is important, as few reports with limited substrate scope are available for such excellent oxidative cleavage of conjugated dienes.

General Olefin Synthesis by the Palladium-Catalyzed Heck Reaction of Amides: Sterically Controlled Chemoselective N-C Activation

Metal-catalyzed reactions of amides proceeding via metal insertion into the N-CO bond are severely underdeveloped due to resonance stabilization of the amide bond. Herein we report the first Heck reaction of amides proceeding via highly chemoselective N-CO cleavage catalyzed by Pd0 utilizing amide bond ground-state destabilization. Conceptually, this transformation provides access to a myriad of metal-catalyzed transformations of amides via metal insertion/decarbonylation.

Cyanuric chloride-dimethylformamide mediated cleavage of cyclopropylcarbinols-synthesis of phenolic antioxidant and construction of a new vinylcyclopropane skeleton

Differently substituted cyclopropylcarbinols underwent ring cleavage with easily accessible cyanuric chloride-N,N-dimethylformamide adduct to produce homoallylic chlorides or dienes depending on the nature and location of the substituents. A mechanistic explanation of the aforesaid observations has been provided. A promising antioxidant compound was prepared following this protocol and studied against Fenton's reagent. This methodology was utilized to construct hitherto unreported vinylcyclopropane frameworks bearing homoallylic chloride and diene moieties.

Effect of substituents and conjugated chain length on the UV spectra of α,ω-di-substituted phenyl polyenes

A series of α,ω-di-substituted phenyl polyenes, p-X-Ph(CH = CH)nPh-p-Y (n = 1, 2, or 3) were synthesized, and their ultraviolet (UV) absorption maximum wavelength were determined. The correlation between molecular structure and the maximum wavelength energy (wavenumber/cm -1) was carried out. The results show that the maximum wavelength energy of the title compounds is mainly affected by both substituent excited-state parameters and maximum wavelength energy of the parent molecule. However, the two influence factors are not independent, and the action of substituent is governed by the parent molecular absorption energy. In the case of the compounds containing NO2 or NH2 groups, the influence of interaction of polarity parameters on the maximum wavelength energy must also be considered. In addition, the exploration was also made for the quantifying correlation of UV absorption maximum wavelength energy with the conjugated polarizability potential CPP replacing the parent molecular absorption energy. And the results indicate that the equation with CPP parameters is more accurate and convenient. Copyright 2013 John Wiley & Sons, Ltd. For the α,ω-di-substituted phenyl polyenes, p-X-Ph(CH = CH)nPh-p-Y (n = 1, 2, or 3), their ultraviolet absorption maximum wavelength energy (wavenumber/cm-1) was mainly affected by both substituent excited-state parameters and maximum wavelength energy of the parent molecule. However, the two influence factors are not independent, and the action of substituent is governed by the parent molecular absorption energy. Copyright

Syntheses of p-terphenyls and 11,12-dihydroindeno[2,1-a]fluorene by one-pot benzannulation of Diels-Alder reactions of trans-1,2-dichloroethene and dienes

A series of substituted p-terphenyls and 11,12-dihydroindeno[2,1-a]fluorene were successfully synthesized by one-pot benzannulation of Diels-Alder reaction with 1,2-dichloroethene as an acetylene equivalent dienophile. Two chlorine atoms could be good leaving groups to easily undergo subsequent elimination reactions of Diels-Alder products at a high temperature.

Finding more active antioxidants and cancer chemoprevention agents by elongating the conjugated links of resveratrol

Resveratrol is the subject of intense research as a natural antioxidant and cancer chemopreventive agent. There has been a great deal of interest and excitement in understanding its action mechanism and developing analogs with antioxidant and cancer chemoprevention activities superior to that of the parent compound in the past decade. This work delineates that elongation of the conjugated links is an important strategy to improve the antioxidant activity of resveratrol analogs, including hydrogen atom- or electron-donating ability in homogeneous solutions and antihemolysis activity in heterogeneous media. More importantly, C3, a triene bearing 4,4′-dihydroxy groups, surfaced as an important lead compound displaying remarkably increased antioxidant, cytotoxic, and apoptosis-inducing activities compared with resveratrol.

Synthesis of 1,4-diarylbuta-1,3-dienes through palladium-catalyzed decarboxylative coupling of unsaturated carboxylic acids

It has been found that readily available hydroxylated cinnamic acids such as ferulic acid undergo palladium-catalyzed decarboxylative coupling with aryl iodides and internal alkynes in a 1:1:1 manner to produce 1,4-diarylbuta-1,3- dienes. The butadiene synthesis has also been achieved through the coupling of aryl halides with dienoic acids. Some of the products exhibit solid-state fluorescence.

Synthesis of α,ω -diarylbutadienes and -hexatrienes via decarboxylative coupling of cinnamic acids with vinyl bromides under palladium catalysis

[Chemical equation presented] Readily available cinnamic acid derivatives such as ferullc acid couple with β-bromostyrenes and 1-bromo-4- phenylbutadiene under palladium catalysis accompanied by decarboxylation to produce the corresponding α,β-diarylbutad