30432-65-6

Upstream product

• 672-65-1 (1-chloroethyl)benzene 
• 103-69-5 N-ethyl-N-phenylamine 
• 82769-48-0 N-ethyl-N-(1-methoxyethyl)aniline 
• 91-66-7 N,N-diethylaniline 
• 98-85-1 1-Phenylethanol 
• 25236-63-9 1-phenylethyl mesylate 
• 32366-25-9 1-azidoethylbenzene 
• 129575-56-0 (R)-α-methylbenzyl azide 
• 536-74-3 phenylacetylene 
• 57818-33-4 N-ethyl-N-(1-phenylethenyl)aniline 
• 538-51-2 benzylidene phenylamine 
• 779-54-4 phenyl(1-phenylethyl)amine 
• 368-39-8 triethyloxonium fluoroborate 

Relevant academic research and scientific papers

Achieving Aliphatic Amine Addition to Arylalkynes via the Lewis Acid Assisted Triazole-Gold (TA-Au) Catalyst System

Transition metal catalyzed intermolecular hydroamination of the arylalkynes with aliphatic amine is generally problematic due to the good coordination between amine and metal cation. With the combination of 1,2,3-triazole coordinated gold(I) catalyst (TA-Au) and Zn(OTf)2 cocatalyst, this challenging transformation was achieved with good to excellent yields and regioselectivity. Compared to previously reported methods, this approach offered an alternative catalyst system to achieve this fundamental chemical transformation with high efficiency and practical conditions.

Ligand-free Iron(II)-Catalyzed N-Alkylation of Hindered Secondary Arylamines with Non-activated Secondary and Primary Alcohols via a Carbocationic Pathway

Secondary benzylic alcohols represent a challenging class of substrates for N-alkylation of amines. Herein, we describe an iron(II)-catalyzed eco-friendly protocol for N-alkylation of secondary arylamines with secondary benzyl alcohols through a carbocationic pathway instead of the known borrowing hydrogen transfer (BHT) approach. Transiently generated carbocations, produced from alcohols via self-condensation, were coupled with arylamines to provide highly functionalized amine products. The scope of this methodology involves N-alkylation of primary, secondary and heterocyclic amines with primary/secondary benzylic, allylic and heterocyclic alcohols, which are common key structures in numerous pharmaceuticals drugs. The method can also be easily adopted for the amination of various natural products. (Figure presented.).

Tin-Catalyzed Selective Reductive Hydroamination of Alkynes for the Synthesis of Tertiary Amines

A unique preference of tin(II) for aniline activation is disclosed. In the present work tin(II) triflate-catalyzed highly selective Markovnikov reductive hydroamination of internal as well as terminal alkynes is reported. The mechanistic study revealed the involvement of two steps in one pot wherein alkyne reduces to corresponding alkene in presence of PMHS as reducing agent followed by hydroamination of alkene. A broad range of alkynes transformed into tertiary amines with good to excellent yield. This method is equally applicable in synthesis of secondary amines.

Zirconium catalysed intermolecular hydroamination reactions of secondary amines with alkynes

An in situ generated cationic zirconium complex stabilized by an n-butylamine-bridged bis(phenolato) ligand has been developed to catalyse hydroamination reactions of secondary amines, which is the first example of group 4 metal based catalysts capable of

A Lewis acid mediated schmidt reaction of benzylic azide: Synthesis of sterically crowded aromatic tertiary amines

An efficient one-pot synthesis of sterically hindered aromatic tertiary amines through Lewis acid induced intermolecular Schmidt reaction of benzylic azides is described. In the presence of EtAlCl2, benzylic azide underwent a smooth Schmidt reaction to give the corresponding iminium ion, which, upon reduction with NaBH4 in situ, afforded the tertiary amine. The effects of substituents on the aromatic ring and the steric effects of the alkyl side chain have also been studied.

Electroorganic Chemistry. 62. Reaction of Iminium Ion with Nuclophile: A Versatile Synthesis of Tetrahydroquinolines and Julolidines

A versatile synthetic method of tetrahydroquinolines and julolidines has been developed.The method involves the anodic oxidation of N,N-dimethylaniline in methanol to afford α-methoxylated or α,α'-dimethoxylated compounds and subsequent treatment of the products with Lewis acids in the presence of nucleophiles.Simple and electron-rich olefins such as alkenes, styrene, enol ethers, silyl enol ethers, enamines, and enol esters are usable as the nucleophiles.The intermediary formation of iminium ions from the methoxylated compounds is proposed as one of the key steps.The nucleophilic reaction od Grignard reagents with the methoxylated compounds in the presence of Lewis acid is also described.

Alkylation of Benzothiazolines and the Stevens Rearrangement of the Resulting 2,3,3-Trisubstituted Benzothiazolinium Salts

Alkylation of 2-substituted 3-methyl- or 3-ethylbenzothiazolines with Meerwein reagents gave 2-substituted 3,3-dialkylbenzothiazolinium tetrafluoroborates (3).The configuration of two alkyl groups on the nitrogen was assigned by NMR spectra and NOE measurement.In the Stevens rearrangement of 3 with lithium diisopropylamide ethyl group showed a much larger migratory aptitude (Et:Me>20:1) than methyl group irrespective of the configuration of 3, and cyclic ammonium ylide with planar ?-type carbanion was proposed as an intermediate. 3 suffered nucleophilic attack at the ring sulfur atom by butyllithium to afford a ring-opened ammonium ylide, which collapses to a radical pair to give unusual Stevens rearrangement product, where o-alkylthiophenyl group migrated selectively in preference to alkyl group, because of stabilization by participation of o-alkylthio group.

Manufacture of arylamines

Arylamines are manufactured by reacting alcohols with amines in the presence of phosphorus-III compounds. The arylamines I manufactured by the process of the invention are intermediates for the manufacture of crop protection agents, optical brighteners, especially amino-coumarin derivatives, and dyes, especially of the xanthene, pyronine, rhodamine, oxazine, azo, triphenylmethane and diphenylmethane series.