217947-24-5

Upstream product

• 4383-23-7 1-phenyl-but-3-enylamine 
• 98-09-9 benzenesulfonyl chloride 
• 13909-34-7 N-benzylidenephenylsulfonamide 
• 106-95-6 allyl bromide 
• 130552-90-8 (E)-N-benzylidenebenzenesulfonamide 
• 762-72-1 allyl-trimethyl-silane 
• 220302-07-8 (Z)-3-bromo-1-iodopropene 
• 591-87-7 Allyl acetate 
• 107-05-1 3-chloroprop-1-ene 
• 24850-33-7 allyltributylstanane 
• 75-16-1 methylmagnesium bromide 
• 98-10-2 benzenesulfonamide 
• 100-52-7 benzaldehyde 
• 1730-25-2 allylmagnesium bromide 

Downstream Products

• 4383-23-7 1-phenyl-but-3-enylamine 
• 13909-34-7 N-benzylidenephenylsulfonamide 

Relevant academic research and scientific papers

Palladium-catalyzed electrophilic substitution of allyl chlorides and acetates via bis-allylpalladium intermediates

Palladium-catalyzed electrophilic allylic substitution of functionalized allyl chlorides and allyl acetates can be achieved in the presence of hexamethylditin under mild and neutral reaction conditions. This efficient one-pot procedure involves palladium-catalyzed formation of transient allylstannanes followed by generation of a bis-allylpalladium intermediate, which subsequently reacts with electrophiles. Using this catalytic transformation, various aldehydes and imines can be allylated providing highly functionalized homoallyl alcohols and amines. Furthermore, tandem bis-allylation reactions could be performed by employing tosyl isocyanate and benzylidenemalonitrile as substrates. A particularly interesting mechanistic feature of this reaction is that palladium catalyzes up to three different transformations in each catalytic cycle. Various allylic functionalities, including COOEt, CONH2, COCH3, CN, Ph, and CH3, are tolerated in the catalytic reactions due to the application of neutral and mild reaction conditions. The substitution reaction occurs with very high regioselectivity at the branched allylic terminus. Moreover, in several reactions, a high stereoselectivity was observed indicating that this new catalytic process has a high potential for stereoselective synthesis. The regioselectivity of the reaction can be explained on the basis of DFT calculations. These studies indicate that the allylic substituent prefers the γ-position of the η1-allyl moiety of the reaction intermediate.

Organometallic reactions in aqueous media. Indium- and zinc-mediated allylation of sulfonimines

Sulfonimines derived from aryl and nonenolizable aliphatic aldehydes can be effectively allylated to the corresponding homoallylic sulfonamides with allylic bromides promoted by indium or zinc. The solvent used can be water, THF, or a mixed aqueous THF solvent. The regioselectivity and stereoselectivity of the reaction were studied.

A Mechanochemical Zinc-Mediated Barbier-Type Allylation Reaction under Ball-Milling Conditions

A ball-milling-enabled zinc-mediated Barbier-type allylation reaction is reported. Notably, running the reaction in this manner renders it effective irrespective of the initial morphology of the zinc metal. The process is operationally simple, does not re

Nitroxyl-Radical-Catalyzed Oxidative Coupling of Amides with Silylated Nucleophiles through N-Halogenation

A nitroxyl-radical-catalyzed oxidative coupling reaction between amines with an N-protecting electron-withdrawing group (EWG) and silylated nucleophiles was developed to furnish coupling products in high yields, thus opening up new frontiers in organocatalyzed reactions. This reaction proceeded through the activation of N-halogenated amides by a nitroxyl-radical catalyst, followed by carbon–carbon coupling with silylated nucleophiles. Studies of the reaction mechanism indicated that the nitroxyl radical activates N-halogenated amides, which are generated from N-EWG-protected amides and a halogenation reagent, to give the corresponding imines.

Assembly of homoallylamine derivatives through iron-catalyzed three-component sulfonamidoallylation reaction

An efficient FeCl3-catalyzed three-component reaction between aldehydes, sulfonamides and allylsilanes has been achieved, which provides a convenient, atom-economic and green way to construct homoallylamine derivatives. In addition, this reaction exhibits excellent syn stereoselectivity with γ-substituted allylsilanes. A practical three-component cascade process to homoallylamine derivatives is reported, which uses cheap and environmentally benign FeCl3 as catalyst and shows excellent syn stereoselectivity with γ-substituted allylsilanes.

Pd-containing organopolyoxometalates derived from Dawson polyoxometalate [P2W15V3O62]9-: Lewis acidity and dual site catalysis

Grafting of a palladium complex to the Dawson vanadotungstate polyanion [P2W15V3O62]9- via an organic ligand generates a large family of pincer-type hybrid polyoxometalates. The palladium-POM derivatives have dual catalytic properties. Unlike their parent inorganic polyanions, they catalyze allylations while retaining their oxidant character, which leads to single-pot dual site catalysis. This opens a new route for multicatalytic reactions.

PCN- and PCS-pincer palladium complexes as tandem catalysts in homoallylation reactions

Novel PCN- and PCS-pincer palladium complexes 2-(dimethylamino)methyl-5- methoxy-6-(diphenylphosphinoxy)phenylpalladium(II) bromide (1), 2-(phenylimino)-5-methoxy-6-(diphenylphosphinoxy)phenylpalladium(II) bromide (2), 2-(phenylthiomethyl)-5-methoxy-6-(di

Phosphomolybdic acid-catalyzed efficient three-component reaction: A facile synthesis of protected homoallylic amines

A new and efficient phosphomolybdic acid (H3PMo 12O40)-catalyzed three-component reaction of aldehydes, carbamate and allyltrimethylsilane to yield the corresponding protected homoallylic amines in good yields is described.

Allylation of aldehyde and imine substrates with in situ generated allylboronates - A simple route to enatioenriched homoallyl alcohols

Allylation of aldehyde and imine substrates was achieved using easily available allylacetates and diboronate reagents in the presence of catalytic amounts of palladium. This operationally simple one-pot reaction has a broad synthetic scope, as many functionalities including, acetate, carbethoxy, amido and nitro groups are tolerated. The allylation reactions proceed with excellent regio- and stereoselectivity affording the branched allylic isomer. By employment of commercially available chiral diboronates enantioenriched homoallyl alcohols (up to 53 % ee) could be obtained. The mechanistic studies revealed that the in situ generated allylboronates react directly with the aldehyde substrates, however the allylation of the sulfonylimine substrate requires palladium catalysis. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.

N-(3-(4-substituted-1-piperidinyl)-1-phenylpropyl) substituted sulfonamides as NK-3 receptor antagonists

The present invention provides a method of treatment of a subject suffering from a disease, such as schizophrenia, for which the administration of an NK-3 antagonist is indicated which comprises administering to that subject a therapeutically effective amount of a compound of formula I: wherein, generally, Q is R1 is benzyl, phenyl, thiophene or imidazolyl optionally substituted with C1-4alkyl or halogen, such as methyl, fluorine or bromine; R2 is hydrogen or C1-4alkyl such as methyl; R3 is phenyl; R4 is hydrogen; R5 is hydrogen or C1-6alkylcarbonyl such as methylcarbonyl; X is —SO2— or —C(O)N(R2)SO2— where R2 is preferably hydrogen; Y is a bond, CH2 or Z1 where Z1 is —N(Rf)— in which Rf is C1-6alkylcarbonyl such as ethylcarbonyl; and R6 is phenyl, pyrazolyl, pyridyl, pyrimidinyl or benzimidazolonyl optionally substituted with one or two groups chosen from C1-6alkyl and benzyl, such as methyl, ethyl and benzyl; or a pharmaceutically acceptable salt thereof.