19618-37-2

Upstream product

• 4356-69-8 1,1-bis-(4-methoxyphenyl)ethylene 
• 93-61-8 N-methyl-N-phenylformamide 
• 7020-80-6 acetaldehyde N-tert-butylimine 
• 90-96-0 bis(p-methoxyphenyl)methanone 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 107-02-8 acrolein 
• 101597-25-5 1,1-bis(4-methoxyphenyl)-2-propyn-1-ol 
• 135-19-3 β-naphthol 
• 101018-40-0 1,1-bis(4-methoxyphenyl)prop-2-en-1-ol 
• 696-62-8 para-iodoanisole 
• 123-38-6 propionaldehyde 
• 1600-44-8 1-oxothiolane 

Downstream Products

• 114995-84-5 2-cyano-5,5-bis(4-methoxyphenyl)-2,4-pentadienenitrile 
• 480391-64-8 3,3-bis-(4-methoxy-phenyl)-1-phenyl-prop-2-en-1-ol 
• 22719-63-7 3-(2,2-diphenylvinyl)-1,1,5,5-tetraphenyl-1,4-pentadiene 
• 942517-57-9 4,4-bis-(4-methoxyphenyl)but-3-en-2-ol 
• 114995-85-6 2-<2',2'-bis(4-methoxyphenyl)ethenyl>-6,10-dioxaspiro<4.5>dec-3-ene-1,1-dicarbonitrile 
• 142121-28-6 N-isopropyl 3,3-di(4-methoxyphenyl)-2-propenyl amine 
• 1488-62-6 2,2-bis(4-methoxyphenyl)-2H-benzopyran 
• 17792-18-6 3,3-bis(4-methoxyphenyl)propenoic acid 
• 35582-69-5 bis-3,3-(p-methoxyphenyl)-propionic acid 
• 120553-24-4 (E)-5,5-bis(4-methoxyphenyl)-2,4-pentadienoic acid 
• 480391-65-9 3,3-bis(4-methoxyphenyl)-1-phenylallyl acetate 

Relevant academic research and scientific papers

Synthesis of gold allyloxysulfonium complexes and elimination to form an α,β-unsaturated aldehyde

Treatment of the gold vinyl carbene/allylic cation complex (E)-[(IPr)AuC(H)C(H)C(4-C6H4OMe)2]+ OTf- with sulfoxides at -95 °C formed the corresponding gold allyloxysulfonium complexes [(IPr)AuC(H)(OSR

Deep eutectic solvent-catalyzed Meyer-Schuster rearrangement of propargylic alcohols under mild and bench reaction conditions

The Meyer-Schuster rearrangement of propargylic alcohols into α,β-unsaturated carbonyl compounds has been revisited by setting up an atom-economic process catalyzed by a deep eutectic solvent FeCl3·6H2O/glycerol. Isomerizations take place smoothly, at room temperature, under air and with short reaction times. The unique solubilizing properties of the eutectic mixture enabled the use of a substrate concentration up to 1.0 M with the medium being recycled up to ten runs without any loss of catalytic activity. This journal is

Ionization of gold (γ-methoxy)vinyl complexes generates reactive gold vinyl carbene complexes

Cationic gold vinyl carbene/allylic cation complexes of the form (E)-[(L)AuC(H)C(H)CAr2]+ OTf- {L = IPr, Ar = Ph [(E)-5a], L = IPr, Ar = 4-C6H4OMe [(E)-5b], L = P(t-Bu)2o-biphenyl, Ar = 4-C6H4OMe [(E)-5c]} were generated in solution via Lewis acid-mediated ionization of the corresponding gold (γ-methoxy)vinyl complexes (E)-(L)AuC(H)C(H)C(OMe)Ar2 at or below -95 °C. Complexes (E)-5b and (E)-5c were fully characterized in solution employing multinuclear NMR spectroscopy, which established the predominant contribution of the aurated allylic cation resonance structure and the significant distribution of positive charge into the γ-anisyl rings. Complex (E)-5b reacted rapidly at -95 °C with neutral two-electron, hydride, and oxygen atom donors exclusively at the C1 position of the vinyl carbene moiety and with p-methoxystyrene to form the corresponding vinylcyclopropane. In the absence of nucleophile (E)-5a decomposed predominantly via intermolecular carbene dimerization whereas formation of 1-aryl-5-methoxy indene upon ionization of (Z)-(IPr)AuC(H)C(H)C(OMe)(4-C6H4OMe)2 [(Z)-6b] implicated an intramolecular Friedel-Crafts or electrocyclic Nazarov pathway for the decomposition of the unobserved vinyl carbene complex (Z)-[(IPr)AuC(H)C(H)C(4-C6H4OMe)2]+ OTf- [(Z)-5b].

A Weinreb Amide Based Building Block for Convenient Access to β,β-Diarylacroleins: Synthesis of 3-Arylindanones

Towards the synthesis of symmetrical and unsymmetrical β,β-diarylacroleins for assembling diarylmethine fragments present in biologically important molecules, we have developed a new Weinreb amide (WA) based building block, derived from propiolic acid. The WA functionality present in this compound allowed the sequential addition of various arylmagnesium bromide reagents in a controlled manner. The developed methodology for the access to β,β-diarylacroleins has been utilised for the synthesis of biologically important 3-arylindanone molecules. Synthesis of both symmetrical and unsymmetrical β,β-diarylacrolein and diarylmethine fragments, have been achieved via easily accessible and hitherto unknown Weinreb Amide (WA) based building block 11. The WA functionality allowed the sequential addition of nucleophiles such as arylmagnesium bromide in a controlled manner, which has enabled the synthesis of an important 3-arylindanone molecule.

Domino Reactions Containing Different Types of Heck Reactions for Selective 3,3- and 1,3-Diarylations of Propenol with Aryl Halides by Triple Catalysis

A new domino Heck-isomerization/Saegusa/Heck reaction of propenol with aryl iodides has been developed for the synthesis of 3,3-diaryl propenals by triple transition-metal catalysis. Moreover, we also developed the domino Heck-isomerization/Heck-type reaction of propenol with aryl iodides for the synthesis of 1,3-diaryl propanones by double transition-metal catalysis and the mediation of secondary amine or triple transition metal catalysis and aminocatalysis.

Palladium-catalyzed dehydrogenative β-arylation of simple saturated carbonyls by aryl halides

(Chemical Equation Presented) A versatile palladium-catalyzed synthesis of highly substituted α,β-unsaturated carbonyl compounds has been developed. In contrast to the known Heck-type coupling reaction of unsaturated carbonyl compounds with aryl halides, the present methodology allows the use of stable and readily available saturated carbonyl compounds as the alkene source. In addition, the reaction proceeds well with low catalyst loadings and does not require any expensive metal oxidants or ligands. A variety of saturated aldehydes, ketones, and esters are compatible for the reaction with aryl halides under the developed reaction conditions to afford α,β-unsaturated carbonyl compounds in good to excellent yields. A possible reaction mechanism involves a palladium-catalyzed dehydrogenation followed by Heck-type cross couplings.

Synthesis and reactivity of new rhenium(I) complexes containing iminophosphorane-phosphine ligands: Application to the catalytic isomerization of propargylic alcohols in ionic liquids

[ReBr(CO)5] reacts with the iminophosphorane-phosphine ligands Ph2PCH2P(=NR)Ph2 (R = P(=O)(OEt)2 (1a), P(=O)(OPh)2 (1b), P(=S)(OEt)2 (1c), P(=S)(OPh) 2 (1d), 4-C6F4CHO (1e), 4-C6F 4CN (1f), 4-C5F4N (1g)) affording the neutral complexes [ReBr(κ2-P,X-Ph2PCH2P{=NP(=X) (OR)2}Ph2)(CO)3] (X = O, R = Et (2a), Ph (2b); X = S, R = Et (2c), Ph (2d)) and [ReBr{κ2-P,N-Ph 2PCH2P(=NR)Ph2}(CO)3] (R = P(=O)(OEt)2 (3a), P(=O)(OPh)2 (3b), 4-C6F 4CHO (3e), 4-C6F4CN (3f), 4-C5F 4N (3g)). The reactivity of the cationic complex [Re(κ 3-P,N,S-Ph2PCH2P{=NP(=S)(OPh) 2}Ph2)(CO)3][SbF6] (4d) has been explored allowing the synthesis of the cationic [Re(L)(κ2-P,S- Ph2PCH2P{=NP(=S)(OPh)2}Ph2)(CO) 3][SbF6] (L = acetone (5a), CH3C≡N (5b), pyridine (5c), PPh3 (5d)) and the neutral [ReY(κ2-P, S-Ph2PCH2P{=NP(=S)(OPh)2}Ph2)(CO) 3] (Y = Cl (6a), I (6b), N3 (6c)) complexes. The catalytic activity of complex 4d in the regioselective isomerization of terminal propargylic alcohols HC≡CCR1R2(OH) into α,β-unsaturated aldehydes R1R2C=CHCHO or ketones R3R4C=CR1COMe (if R2 = CHR3R4) under neutral conditions in ionic liquids has being studied. Isolation and X-ray characterization of the key intermediate rhenium(I) oxocyclocarbene complex [Re{=C(CH2)3O} (κ2-P,S-Ph2PCH2P{=NP(=S)(OPh) 2}Ph2)(CO)3][SbF6] (5e) seems to indicate that the catalytic reaction proceeds through tautomerization of the terminal alkynols to yield vinilydene-type species.

Novel rhenium(i) catalysts for the isomerization of propargylic alcohols into α,β-unsaturated carbonyl compounds: An unprecedented recyclable catalytic system in ionic liquids

Carbonyl rhenium(i) complexes are efficient catalysts for the regioselective isomerization of terminal propargylic alcohols into α,β-unsaturated aldehydes or ketones which can be used as an unprecedented recyclable catalytic system (up to 10 consecutive runs) in the ionic liquid [BMIM][PF6].

Palladium-catalyzed oxidative rearrangement of diaryl alkenyl carbinols to β,β-diaryl α,β-unsaturated ketones

An unusual oxidative palladium-catalyzed rearrangement of diaryl alkenyl carbinols to β,β-diaryl α,β-unsaturated ketones is described. The geometry of the alkene product is not determined by the electronic nature of the aryl substitutents but rather is determined by substitution pattern on the aryl rings. The reaction proceeds in good yields, utilizes oxygen at atmospheric pressure as the terminal oxidant, and tolerates a variety of functional groups on the aryl rings.

Microwave-assisted InCl3-catalyzed Meyer-Schuster rearrangement of propargylic aryl carbinols in aqueous media: a green approach to α,β-unsaturated carbonyl compounds

A novel, efficient, simple and environmentally benign protocol for the Meyer-Schuster isomerization of propargylic aryl carbinols into α,β-unsaturated carbonyl compounds has been developed using catalytic amounts of InCl3, pure water as the solvent, and microwave irradiation as the heating source.