439077-71-1

Upstream product

• 51608-60-7 N-(benzylidene)-p-methylbenzenesulfonamide 
• 78-94-4 methyl vinyl ketone 
• 70-55-3 toluene-4-sulfonamide 
• 94348-75-1 4-acetoxy-3-methylene-4-phenylbutan-2-one 
• 51608-60-7 phenyl N-tosyl imine 
• 100-52-7 benzaldehyde 

Downstream Products

• 690985-86-5 N-(2-acetyl-1-phenyl-allyl)-N-allyl-4-methyl-benzenesulfonamide 

Relevant academic research and scientific papers

The Aza-Morita-Baylis-Hillman reaction: A mechanistic and kinetic study

The aza-Morita-Baylis-Hillman (aza-MBH) reaction has been studied in a variety of solvents, a selection of imine substrates and with various combinations of PPh3 and para-nitrophenol as the catalyst system. The measured kinetic data indicates that the effects of solvent and protic co-catalyst are strongly interdependent. These results are most easily reconciled with a mechanistic model involving the reversible protonation of zwitterionic intermediates in the catalytic cycle, which is also supported by 31P NMR spectroscopy and quantum chemical studies. Copyright

Triphenylphosphine Photorelease and Induction of Catalytic Activity from Ruthenium-Arene Complexes Bearing a Photoswitchable o-Tosylamide Azobenzene Ligand

The reactivity of cationic arene ruthenium complexes bearing a photoswitchable o-tosylamide azobenzene ligand toward various phosphorus nucleophiles was investigated. The resulting phosphine-ruthenium complexes containing an azobenzene ligand were isolated as the Z isomer. Under appropriate reaction conditions, quantitative triphenylphosphine photorelease from the complex was achieved through Z → E isomerization of the ligand. This process was applied to the photoinitiation of the catalytic aza-Morita-Baylis-Hillman reaction.

Aza-Morita-Baylis-Hillman reactions catalyzed by a cyclopropenylidene

Catalysis using a bis(dialkylamino)cyclopropenylidene (BAC) has been developed, which relies on a formal umpolung activation of Michael acceptor pro-nucleophiles. Various aza-Morita-Baylis-Hillman reactions between aromatic, heteroaromatic, or aliphatic imines and acyclic or cyclic α,β-unsaturated ketones and carboxylic acid derivatives have been catalyzed by a BAC under mild conditions. Functionalities such as unprotected amino and hydroxy groups have been tolerated. The catalyst loading was decreased to 1 mol% without loss of activity. The BAC catalyst was shown to be substantially more active than a cyclic (alkyl)(amino) carbene (CAAC), N-heterocyclic carbenes (NHCs), and P- or N-centered Lewis bases.

When Chirality Meets “Buchwald-Type” Phosphines: Synthesis and Evaluation in Frustrated Lewis Pair-, Lewis Base- and Palladium-Promoted Asymmetric Catalysis

We describe the synthesis of axially chiral “Buchwald ligand”-like biphenylphosphines in highly enantioenriched form. These monodentate phosphines, biphenyl analogues of Hayashi's MOP ligands, were evaluated in phosphine-promoted organocatalysis and in hydrosilylations catalyzed by palladium or by frustrated Lewis pairs. As expected, the title phosphines appeared best suited for transition metal catalysis where they provided higher asymmetric induction.

Aza-Morita-Baylis-Hillman reaction with ion-supported Ph3P

Various N-tosyl arylimines reacted with methyl vinyl ketone and ethyl vinyl ketone in the presence of ion-supported Ph3P A and B to give adducts, N-(2′-methylene-3′-oxo-1′-arylbutyl)-4- methylbenzenesulfonamides and N-(2′-methylene-3′-oxo-1′- a

2-(Diphenylphosphino)benzoyl-substituted calix[4]arene: Efficient organocatalyst in aza-Morita-Baylis-Hillman reaction of N-sulfonated imines with methyl vinyl ketone

A novel bifunctional organocatalyst 5,11,17,23-tetra-butyl-25-[2- (diphenylphosphino)benzoate]-26,27,28-trihydroxycalix-[4]arene (LB3) was synthesized and applied to promote the aza-Morita-Baylis-Hillman (aza-MBH) reaction of N-sulfonated im-ines with met

The aza-Morita-Baylis-Hillman reaction of electronically and sterically deactivated substrates

The aza-Morita-Baylis-Hillman (azaMBH) reaction has been studied for electronically and sterically deactivated Michael acceptors. It is found that electronically deactivated systems can be converted with electron-rich phosphanes and pyridines as catalysts

Immobilized DMAP derivatives rivaling homogeneous DMAP

The copper-catalyzed Huisgen reaction between azides and alkynes was utilized to covalently attach derivatives of 4-(dimethylamino)pyridine (DMAP) to a polystyrene resin (PS) support. The catalytic potential of these constructs as determined in acylation and aza-Morita-Baylis-Hillman reactions far exceeds that of commercially available DMAP-PS resins and is fully competitive with DMAP in homogeneous solution. Immobilization of 3,4-diaminopyridine catalysts on polystyrene by using the copper-catalyzed Huisgen reaction allowed the preparation of new supported catalysts ofunprecedented catalytic activity in acylation and aza-Morita-Baylis-Hillman reactions. Copyright

First application of air-stable and reusable phosphine-containing calix[4]arene in catalytic aza-morita-baylis-hillman reaction

For the first time, the aza-Morita-Baylis-Hillman reaction of N-sulfonated imines with methyl vinyl ketone was catalyzed by 5,11,17,23-tetrabutyl-25- (diphenylphosphinomethoxy)-26,27,28-trihydroxycalix[4]arene (LB1), an air-stable, easily isolated and reu

1,3,5-triaza-7-phosphaadamantane (PTA): A practical and versatile nucleophilic phosphine organocatalyst

In this paper, the air-stable and readily available 1,3,5-triaza-7- phosphaadmantane (PTA) is reported as a practical and versatile nucleophilic phosphine organocatalyst. Under the mediation of 15-30 mol% of PTA, various electrophiles like aldehydes and i