35755-80-7

Upstream product

• 106-99-0 buta-1,3-diene 
• 62-53-3 aniline 
• 146514-07-0 (E)-but-2-en-1-yl phenylcarbamate 
• 100-65-2 N-Phenylhydroxylamine 
• 123-73-9 trans-Crotonaldehyde 
• 504-61-0 (E)-but-2-enol 
• 121197-99-7 crotyl tripropyl pyrophosphate 
• 69611-44-5 N-(3-methyl-2-butyne)aniline 
• 4784-77-4 (E)-1-Bromo-2-butene 
• 17304-01-7 tricrotylborane 
• 103185-13-3 (E)-crotyl methyl carbonate 
• 941278-25-7 (E)-but-2-en-1-yl tert-butyl carbonate 
• 591-50-4 iodobenzene 
• 107733-62-0 benzyl crotyl amine 

Downstream Products

• 115914-05-1 N-butenyl-N-phenyl-2-phenyl-1-propenylamine 
• 16327-64-3 [(E)-2-Methyl-2-phenyl-hex-4-en-(E)-ylidene]-phenyl-amine 
• 150630-83-4 N-(2-trans-Butenyl)-N-phenyl-1-amino-2-acetophenone 
• 120346-52-3 3-methyl-1-phenyl-1H-pyrrol-2(5H)-one 
• 150630-67-4 N-(2-trans-Butenyl)-N-phenyl-1-amino-2-acetophenone oxime 
• 1245920-63-1 C₁₇H₂₀N₂O₂S 

Relevant academic research and scientific papers

A Simple, Broad-Scope Nickel(0) Precatalyst System for the Direct Amination of Allyl Alcohols

The preparation of allylic amines is traditionally accomplished by reactions of amines with reactive electrophiles, such as allylic halides, sulfonates, or oxyphosphonium species; such methods involve hazardous reagents, generate stoichiometric waste streams, and often suffer from side reactions (such as overalkylation). We report here the first broad-scope nickel-catalysed direct amination of allyl alcohols: An inexpensive NiII/Zn couple enables the allylation of primary, secondary, and electron-deficient amines without the need for glove-box techniques. Under mild conditions, primary and secondary aliphatic amines react smoothly with a range of allyl alcohols, giving secondary and tertiary amines efficiently. This “totally catalytic” method can also be applied to electron-deficient nitrogen nucleophiles; the practicality of the process was demonstrated in an efficient, gram-scale preparation of the calcium antagonist drug substance flunarizine (Sibelium).

Synthetic method of allylamine

The invention provides a synthetic method of allylamine compounds with substituted allyl alcohol and aromatic amines as raw materials through induction of a titanium metal intermediate. The invention relates to a secondary amine substituted by an allyl gr

Synthesis of a leucomitosane via a diastereoselective radical cascade

The preparation of trans-2,3-disubstituted indolines from 1-azido-2-allylbenzene derivatives via a diastereoselective radical cascade using ethyl iodoacetate and triethylborane is described. Further lactamization afforded substituted benzopyrrolizidinones

Modular synthesis of 1,2-Diamine derivatives by palladium-Catalyzed aerobic oxidative cyclization of allylic sulfamides

Chemical equation presented Allylic sulfamides undergo aerobic oxidative cyclization at room temperature, mediated by a Pd(O 2CCF3)2/DMSO catalyst system in tetrahydrofuran. The cyclic sulfamide products are readily converted into 1,2-diamines, and substrates derived from chiral allylic amines cyclize with very high diastereoselectivity.

Platinum-catalyzed direct amination of allylic alcohols under mild conditions: Ligand and microwave effects, substrate scope, and mechanistic study

Transition metal-catalyzed amination of allylic compounds via a π-allylmetal intermediate is a powerful and useful method for synthesizing allylamines. Direct catalytic substitution of allylic alcohols, which forms water as the sole coproduct, has recently attracted attention for its environmental and economical advantages. Here, we describe the development of a versatile direct catalytic amination of both aryl- and alkyl-substituted allylic alcohols with various amines using Pt-Xantphos and Pt-DPEphos catalyst systems, which allows for the selective synthesis of various monoallylamines, such as the biologically active compounds Naftifine and Flunarizine, in good to high yield without need for an activator. The choice of the ligand was crucial toward achieving high catalytic activity, and we demonstrated that not only the large bite-angle but also the linker oxygen atom of the Xantphos and DPEphos ligands was highly important. In addition, microwave heating dramatically affected the catalyst activity and considerably decreased the reaction time compared with conventional heating. Furthermore, several mechanistic investigations, including 1H and 31P{1H} NMR studies; isolation and characterization of several catalytic intermediates, Pt(xantphos)Cl2, Pt(η2-C3H5OH)(xantphos), etc; confirmation of the structure of [Pt(η3-allyl)(xantphos)]OTf by X-ray crystallographic analysis; and crossover experiments, suggested that formation of the π-allylplatinum complex through the elimination of water is an irreversible rate-determining step and that the other processes in the catalytic cycle are reversible, even at room temperature.

Synthesis of secondary amines by titanium-mediated transfer of alkenyl groups from alcohols

Reaction of Ti(NMe2)4 with allyl alcohols and primary amines leads to the selective formation of secondary allylic amines. The allyl transfer from the alcohol to the amine occurs with selective allylic transposition. Due to substituent effects in the reactions, we postulate that the reaction occurs through a [2 + 2]/retro-[2 + 2]-cycloaddition mechanism. It was also found that a similar reaction could be accomplished with homoallylic alcohol. In this case, the more complex mechanism leads to the formation of 1-aza-spiro[5.5]undecane. Possible pathways for the homoallylic transfer and cyclization are discussed. Copyright

Regioselective iron-catalyzed allylic amination

(Chemical Equation Presented) Iron age: An air- and water-resistant iron(-II) catalyst, in the presence of triphenylphosphane under buffered conditions, allows for the highly regioselective and stereoselective allylation of primary aromatic amines. A broa

Efficient C-N bond formations catalyzed by a proton-exchanged montmorillonite as a heterogeneous Bronsted acid

Nucleophilic addition of sulfonamides and carboxamides to simple alkenes proceeded smoothly using a proton-exchanged montmorillonite catalyst. The spent catalyst was recovered easily from the reaction mixture and was reusable at least five times without any loss of activity. The unique acidity of the proton-exchanged montmorillonite (H-mont) catalyst was found to be applicable to additional reactions: substitution of hydroxyl groups of alcohols with amides and anilines.

Efficient protocol for reductive amination of aldehydes and ketones with sodium borohydride in an ionic liquid/H2O system

The imines were generated in situ from carbonyl compounds and amines, which undergo smooth reduction with sodium borohydride in an ionic liquid/H 2O solvent system. The reaction conditions were very mild and neutral to afford the corresponding highly functionalized amines in excellent yields. Copyright Taylor & Francis Group, LLC.

Ruthenium-catalyzed intermolecular coupling reactions of arylamines with ethylene and 1,3-dienes: Mechanistic insight on hydroamination vs ortho-C-H bond activation

(Chemical Equation Presented) The cationic ruthenium complex [(PCy 3)2(CO)(Cl)Ru=CHCH=C(CH3)2] +BF4- was found to be an effective catalyst for the coupling reaction of aniline and ethylene to form a ～1:1 ratio of N-ethylaniline and 2-methylquinoline products. The analogous reaction with 1,3-dienes resulted in the preferential formation of Markovnikov addition products. The normal isotope effect of kNH/kND = 2.2 (aniline and aniline-d7 at 80°C) and the Hammett ρ = -0.43 (correlation of para-substituted p-X-C6H4NH2) suggest an N-H bond activation rate-limiting step for the catalytic reaction.