120553-80-2

Upstream product

• 14371-10-9 (E)-3-phenylpropenal 
• 696-62-8 para-iodoanisole 
• 104-54-1 3-Phenylpropenol 
• 104-55-2 3-phenyl-propenal 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 13632-62-7 1-(4-methoxyphenyl)-1-phenyl-2-propyn-1-ol 
• 4333-75-9 1-(4-methoxyphenyl)-1-phenylethene 
• 75-27-4 bromodichloromethane 
• 611-94-9 4-Methoxybenzophenone 
• 2216-94-6 phenylpropynoic acid ethyl ester 
• 5720-07-0 4-methoxyphenylboronic acid 
• 7020-80-6 acetaldehyde N-tert-butylimine 
• 14063-79-7 3-chloro-3-(4-methoxyphenyl)acrylaldehyde 
• 98-80-6 phenylboronic acid 

Downstream Products

• 863970-18-7 (R)-3-(4-methoxyphenyl)-3-phenylpropanal 
• 92804-32-5 (S)-3-(4-methoxyphenyl)-3-phenylpropanal 
• 120554-56-5 (E,E)-5-(4-methoxyphenyl)-5-phenyl-2,4-pentadienoic acid 4-nitrophenyl ester 
• 120555-51-3 (E,E)-5-(4-methoxyphenyl)-5-phenyl-2,4-pentadienoic acid 
• 1393641-94-5 2-(4-methoxyphenyl)-2-phenyl-2H-benzopyran 

Relevant academic research and scientific papers

Selenated NHC-Pd(II) catalyzed Suzuki-Miyaura coupling of ferrocene substituted β-chloro-cinnamaldehydes, acrylonitriles and malononitriles for the synthesis of novel ferrocene derivatives and their solvatochromic studies

Suzuki-Miyaura coupling reaction between ferrocenyl/phenyl derivatives of (2-formyl-1-chlorovinyl)ferrocene, 3-chloro-3-ferrocenylacrylonitrile and (3-chloro-3-ferrocenylallylidene)malononitrile and arylboronic acid in the catalytic presence of a selenated NHC-Pd(II) full pincer complex was accomplished. Significantly, the couplings take place in water under normal atmospheric conditions, in contrast to many earlier reported Pd-catalysed reactions requiring inert atmosphere conditions. Solvatochromic studies of new ferrocene compounds revealed some interesting changes. Aggregation studies showed an increase of the absorbance with decrease of water content in the water/DMSO solvent mixture.

Mizoroki–Heck reaction of 1,2-disubstituted aryl alkenes: Variables of synthesis, solvent and ligand modulation of reactivity

Reaction of aryl iodides with 1,2-disubstituted aryl alkenes in the presence of TBABr/TBACl gave high yields of the Mizoroki–Heck product. Phosphine ligands were used for the modulation of reactivity and stereoselectivity, for the reaction of 4-iodoanisole with cinnamaldehyde. tert-Bu3P.HBF4 gave the highest E:Z ratio of 1:0.08. The use of PEG-200 and PEG-400 as solvent could activate the reaction of aryl iodides with various 1,2-disubstituetd aryl alkenes.

Copper-catalyzed formylation of alkenyl C-H bonds using BrCHCl2 as a stoichiometric formylating reagent

The first example of copper-catalyzed direct formylation of alkenyl C-H bonds for the facile synthesis of α,β-unsaturated aldehydes has been developed. This transformation has demonstrated high reactivity, mild reaction conditions and a broad substrate scope. BrCHCl2 is expected to be developed as an efficient stoichiometric C1 building block in organic synthesis.

Silver sequestration of halides for the activation of Pd(OAc)2 catalyzed Mizoroki-Heck reaction of 1,1 and 1,2 - Disubstituted alkenes

A ligand free catalytic system consisting of Pd(OAc)2 (cat) and stoichiometric quantities of silver salts, AgOAc or AgBF4, exhibit high efficiency in the Mizoroki-Heck arylation, transforming aryl iodides and 1,1 as well as 1,2 disubstituted alkenes into 1,1,2 – trisubstituted aryl alkenes in excellent yields in very short reaction times.

Metal- and Acid-Free Methyl Triflate Catalyzed Meyer-Schuster Rearrangement

A novel metal- and acid-free preparation of synthetically useful α,β-unsaturated carbonyl compounds from propargyl alcohols has been realized. This Meyer-Schuster rearrangement process is effectively catalyzed by methyl triflate (20 mol%) to prepare a broad scope of conjugated E -enals and E -enones generally in good to excellent yields (up to 90%). This reaction procedure operates under mild conditions (70 °C), in air, with short reaction times (1 h). Moreover, a carbocation intermediate trapped by the solvent 2,2,2-trifluoroethanol was isolated during this transformation.

Asymmetric Traceless Petasis Borono-Mannich Reactions of Enals: Reductive Transposition of Allylic Diazenes

The traceless Petasis borono-Mannich reaction of enals, sulfonylhydrazines, and allylboronates, catalyzed by chiral biphenols, results in an asymmetric reductive transposition of the in situ generated allylic diazene. Acyclic 1,4-diene products bearing either alkyl- or aryl-substituted benzylic stereocenters are afforded in excellent yields and enantiomeric ratios of up to 99:1. The use of crotylboronates in the reaction results in concomitant formation of two stereocenters in either a 1,4-syn or anti relationship from the corresponding E- or Z-crotylboronate used in the reaction. The use of β-monosubstituted enals in the asymmetric traceless Petasis borono-Mannich reaction of crotylboronates installs tertiary methyl-bearing stereocenters in good yields and high enantioselectivities.

[PF6]2 As catalyst for the meyer-schuster rearrangement of arylpropargylic alcohols under mild conditions

The novel iridium complex [IrCpNCMe2PPh2Me][PF6]2 I efficiently catalyzed the Meyer-Schuster rearrangement of selected arylpropargylic alcohols into α,β-unsaturated aldehydes under mild conditions and without the need of a co-catalyst. A mechanism involving a hydroxy alkenylcarbene intermediate is proposed. [IrCpNCMe2PPh2Me][PF6]2 efficiently catalyzes the rearrangement of propargylic alcohols into α,β-unsaturated aldehydes under mild conditions and without the need of a co-catalyst.

Pd-arylurea complexes for the Heck arylation of crotonic and cinnamic substrates

A catalyst consisting of the 1:2 complex of Pd(OAc)2 (1 mol %) with N-(4-carbethoxy)-phenylurea promotes the Heck arylation of a range of crotonic and cinnamic substrates, including aldehydes, ketones, esters, and nitriles, with electron-rich - but not electron-deficient - aryl iodides.

Selective reactivity of electron-rich aryl iodides in the Heck arylation of disubstituted alkenes catalyzed by palladium-arylurea complexes

A catalyst consisting of 1 mol % of the 1:2 complex of Pd(OAc)2 with N-(4-carbethoxyphenyl)urea promotes the Heck arylation of 2- or 3-substituted, conjugated esters, nitriles, aldehydes, and ketones (an uncharacteristically broad range of substrates), but only with electron-rich aryl iodides (an uncharacteristically narrow range of halides).

Chiral dihydrobenzo[1,4]oxazines as catalysts for the asymmetric transfer-hydrogenation of α,β-unsaturated aldehydes

A new class of organocatalysts based on the structure of 2,3-dihydrobenzo[1,4]oxazine was prepared and applied in the enantioselective transfer-hydrogenation of α,β-unsaturated aldehydes with Hantzsch ester as hydride donor. These catalysts proved to be particularly effective for the conjugate reduction of β,β-diaryl-substituted acrylaldehydes leading to saturated aldehydes bearing a stereogenic center with two different aryl groups with enantioselectivities of up to 91% ee.