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• 110-91-8 morpholine 
• 78-79-5 isoprene 
• 556-82-1 3-methyl-2-buten-1-ol 
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• 106625-71-2 ethyl (2-methylbut-3-en-2-yl) carbonate 
• 54664-07-2 1-(2-diphenylphosphinoylethyl)morpholine 
• 1191-16-8 3-methylbut-2-enyl acetate 
• 85620-71-9 3-diphenylphosphinoyl-2-methyl-4-morpholinobutan-2-ol 

Relevant academic research and scientific papers

Cationic [(Iminophosphine)Nickel(Allyl)]+Complexes as the First Example of Nickel Catalysts for Direct Hydroamination of Allenes

The first example of nickel-catalyzed hydroamination of allenes is reported. The new cationic [(3-iminophosphine)nickel(allyl)]+catalysts have been fully characterized and act regioselectively in the catalytic hydroamination of allenes with sec

N-heterocyclic carbene C,S palladium(II) π-allyl complexes: Synthesis, characterization, and catalytic application in allylic amination reactions

A series of five-membered N-heterocyclic carbene C,S palladium(II) π-allyl complexes were successfully developed and characterized. Structural analyses of these complexes revealed that the organopalladium chelates adopt a skew-envelope conformation with a

Isoprene hydroamination catalyzed by palladium xantphos complexes

Pd(II) Xantphos or Xantphos chalcogenide complexes with general folmula [PdCl2(X∩X)] (where X = P, O, S or Se) were synthesized by the addition of corresponding ligands to [PdCl2(COD)] (COD = 1,5-cyclooctadiene). Prepared Complexes [

Palladium(II) 3-iminophosphine (3IP) complexes: Active precatalysts for the intermolecular hydroamination of 1,2-dienes (allenes) and 1,3-dienes with aliphatic amines under mild conditions

The synthesis of alicyclic 3-iminophosphine ligands is extended to include a new framework incorporating a cyclohexenyl backbone with an N-aryl imino functionality (3IPAr). Accordingly, a series of palladium(II) complexes employing this new lig

Gold-catalyzed intermolecular markovnikov hydroamination of allenes with secondary amines

A cationic (CAAC)gold(I) complex promotes the addition of all types of nontertiary amines to a variety of alienes, affording allylic amines in good to excellent yields; the amino fragment always adds to the less substituted terminus of the CCC skeleton.

GOLD CATALYZED HYDROAMINATION OF ALKYNES AND ALLENES

Methods are provided for the catalytic hydroamination of compounds having an alkyne or allene functional group, in which the compound is contacted with ammonia or an amine in the presence of a catalytic amount of a gold complex under conditions sufficient for hydroamination to occur.

New insights into the mechanism of palladium-catalyzed allylic amination

A comparative investigation into palladium-catalyzed allylic amination of unsubstituted aziridines and secondary amines has been carried out. The use of NH aziridines as nucleophiles favors formation of valuable branched products in the case of aliphatic allyl acetates. The regioselectivity of this reaction is opposite to that observed when other amines are used as nucleophiles. Our study provides evidence for the palladium-catalyzed isomerization of the branched (kinetic) product formed with common secondary amines into the thermodynamic (linear) product. In contrast, the branched allyl products obtained from unsubstituted aziridines do not undergo the isomerization process. Crossover experiments indicate that the isomerization of branched allylamines is bimolecular and is catalyzed by Pd0. The reaction has significant solvent effect, giving the highest branched-to-linear ratios in THF. This finding can be explained by invoking the intermediacy of σ-complexes, which is consistent with NMR data. The apparent stability of branched allyl aziridines towards palladium-catalyzed isomerization is attributed to a combination of factors that stem from a higher degree of s-character of the aziridine nitrogen compared to other amines. The reaction allows for regio- and enantioselective incorporation of aziridine rings into appropriately functionalized building blocks. The resulting methodology addresses an important issue of forming quaternary carbon centers next to nitrogen. The new insights into the mechanism of palladium-catalyzed allylic amination obtained in this study should facilitate synthesis of complex heterocycles, design of new ligands to control branched-to-linear ratio, as well as absolute stereochemistry of allylamines.

Reactions of Isoprene with Secondary Amines

Reactions of isoprene with secondary amines in the presence of alkali metals yield isomeric aminoolefins: 1-dialkylamino-3-methyl-2-butenes, 1-dialkylamino-2-methyl-2-butenes, and 1-dialkylamino-3-methyl-1-butenes.The influence of temperature, structure of the secondary amine, amount of catalyst, and molar ratio of the reactants on the yield of aminoolefins and selectivity of their formation has been examined.

REGIO- AND STEREOSPECIFIC SYNTHESIS OF ALLYLIC TERTIARY AMINES

E and Z allylic amines have been synthesised by stereospecific elimination of Ph2PO2- from pure diastereoisomers (3) and (4).