6045-18-7

Upstream product

• 100-61-8 N-methylaniline 
• 513-42-8 3-hydroxy-2-methyl-1-propene 
• 614-30-2 N-methyl-N-phenyl-benzenemethanamine 
• 1458-98-6 2-methyl-3-bromo-1-propene 
• 78-85-3 2-methylpropenal 
• 2739-12-0 N-methylaniline hydrochloride 
• 13291-18-4 isopropenylmagnesium bromide 
• 15497-51-5 N-((1H-benzo(d)(1,2,3)triazol-1-yl)methyl)-N-methylaniline 
• 563-47-3 3-Chloro-2-methylpropene 
• 18292-38-1 2-methallyltrimethylsilane 

Downstream Products

• 78191-65-8 (N-methyl N-phenylamino)-3 methyl-2 propanol-1 
• 18023-32-0 1,2,2-trimethyl-2,3-dihydro-indole 
• 41652-75-9 2-(2-methyl-2-propenyl)-N-methylaniline 
• 93-61-8 N-methyl-N-phenylformamide 
• 59158-97-3 2-methyl-4,4-diphenylbut-3-enoic acid methyl ester 

Relevant academic research and scientific papers

A facile and expedient route to allyl and propargyl amines using N-(α-Benzotriazolylalkyl) amines as stabilized iminium salts

N-(α-Benzotriazolylalkyl)amines 1a-g serve as stabilized iminium salts for the preparation of allylamines 3a-i in 82-94% yield in two steps starting from benzotriazole, an amine, an aldehyde, and the corresponding vinyl Grignard. Propargylamines 7a-e were

Visible light-induced N-methyl activation of unsymmetric tertiary amines

In the presence of methylene group, selective N-methyl activation of tertiary amines has been accomplished with the aid of visible light using organic photocatalyst under air. This protocol explores numerous aliphatic and aromatic substituted tetra-hydroquinoline analogues from various tertiary amines and maleimides. Furthermore, this approach was applied to activate the methyl group of N-methyl carbazole to generate the biologically active molecule.

Reactions of Tertiary Allylic Amines and Dichlorocarbenes

In this article, a study on reactions of tertiary allylic amines and dichlorocarbenes had been described. Tertiary allylic amines could result from an interesting de-N-allylation/formylation reaction under the treatment of dichlorocarbenes. Notably, amines containing steric substituents or electron-deficient aromatic substituents on the nitrogen will go through cyclopropanations of the carbon-carbon double bond.

An efficient and convenient palladium catalyst system for the synthesis of amines from allylic alcohols

A novel catalyst system for efficient amination of allylic alcohols with aryl and alkyl amines is presented. By applying a convenient combination consisting of Pd(OAc)2/1,10-phenanthroline, a variety of allylic alcohols reacted smoothly to give the corresponding secondary and tertiary amines in good to excellent yields with high regioselectivity. The usefulness of our protocol is demonstrated in the one-step synthesis of the antifungal drug naftifine and the calcium channel blocker flunarizine. One pot is all it takes: By applying a convenient combination consisting of Pd(OAc)2/1,10- phenanthroline, a variety of allylic alcohols reacts smoothly to give the corresponding secondary and tertiary amines in good to excellent yields with high regioselectivity (see picture).

Highly efficient and regioselective allylic amination of allylic alcohols catalyzed by [Mo3PdS4] cluster

A highly efficient and regioselective allylation reaction of amines with allylic alcohols under mild conditions catalyzed by the cubane-type sulfido cluster [(Cp*Mo)3S4Pd(dba)][PF6] with H3BO3 as an additive has been developed. A variety of amines and allylic alcohols are investigated, and in the case of allylic alcohols bearing substituents at either α- or γ-position only linear allylic amination products are obtained.

Amination of allylic alcohols in water at room temperature

The "trick" to carrying out regiocontrolled aminations of allylic alcohols in water as the only medium is use of a nanomicelle's interior as the organic reaction solvent. When HCO2Me is present, along with the proper base and source of catalytic Pd, allylic amines are cleanly formed at room temperature.

Highly chemoselective reductive amination of carbonyl compounds promoted by InCl3/Et3SiH/MeOH system

(Chemical Equation Presented) A new strategy has been developed for reductive amination of aldehydes and ketones with the InCV Et 3SiH/MeOH system, which is a nontoxic system with highly chemoselective and nonwater sensitive properties. The methodology can be applied to a variety of cyclic, acyclic, aromatic, and aliphatic amines. Functionalities including ester, hydroxyl, carboxylic acid, and olefin are found to be stable under our conditions. The reaction shows a first-order kinetics profile with respect to both InCl3 and Et3SiH. Spectroscopic techniques such as NMR and ESI-MS have been employed to probe the active and resulting species arising from InCl3 and Et3SiH in MeOH, which are important in deriving a mechanistic proposal. In the ESI-MS studies, we have first discovered the existence of stable methanol-coordinated indium(III) species which are presumably responsible for the gentle generation of indium hydride at room temperature. The solvent attribution was crucial in tuning the reactivity of [In-H] species, leading to the establishment of mild reaction conditions. The system is superior in flexible tuning of hydride reactivity, resulting in the system being highly chemoselective.

Pd·Et3B-catalyzed alkylation of amines with allylic alcohols

A combination of catalytic amounts of Pd (0.05 mmol) and Et3B (0.3 mmol) promotes allylic alkylation of primary and secondary aromatic and aliphatic amines (1.0 mmol) by the direct use of allylic alcohols, providing tertiary amines in excellent yields under mild conditions (room temperature ～ 50°C).

Synthesis of γ-amino- and δ-amino-functionalised ethers, amines, or silanes by hydroaminomethylation of heterofunctionalised allylic compounds

Heterofunctionalised allylic ethers 1, silanes 5, and amines 9 are hydroformylated in the presence of primary or secondary amines 2 to form the corresponding γ-amino- and δ-amino-functionalised compounds. The rhodium(I)-catalysed reaction sequence proceeds by aldehyde formation and subsequent reductive amination to generate the corresponding functionalised secondary or tertiary amines. This selective one-pot hydroaminomethylation procedure establishes access to γ-amino- and δ-amino-functionalised ethers, amines or silanes with potential biological activity.

TRANSFORMATION OF ALLYLSILANES INTO ALLYLAMINES VIA PHENYLTELLURINYLATION

Allylsilanes were treated with benzenetellurinyl trifluoracetate below room temperature followed by amines at 65 deg.C in 1,2-dichloroethane in the presence of boron trifluoride etherate, readily giving allylamines.