150562-30-4

Upstream product

• 783-08-4 [4-(benzylideneamino)phenyl]methanol 
• 106-95-6 allyl bromide 
• 24850-33-7 allyltributylstanane 
• 688-61-9 Triallylborane 
• 1613-90-7 4-methoxy-N-[(E)-phenylmethylidene]aniline 
• 1730-25-2 allylmagnesium bromide 
• 70286-37-2 4-methoxybenzaldehyde O-methyl oxime 
• 591-51-5 phenyllithium 
• 100-52-7 benzaldehyde 
• 104-94-9 4-methoxy-aniline 
• 911482-75-2 allylboronic acid 2,2-dimethyl-1,3-propanediol ester 
• 54655-41-3 B-allyl-1,3,2-dioxaborinane 
• 100-46-9 benzylamine 
• 72824-04-5 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Downstream Products

• 76403-31-1 (1-Phenyl-but-3-enyl)-carbamic acid methyl ester 
• 4383-23-7 1-phenyl-but-3-enylamine 
• 426825-64-1 (4-methoxy-phenyl)-(1-phenyl-but-3-enyl)-carbamic acid methyl ester 

Relevant academic research and scientific papers

Allylic Tantalums as Highly Imine-Selective Reagents

A pratical method for the allylation of low electrophilic N-aliphatic imines was established by allylic tantalum. This is a superior methodology compared with conventional ones in terms of wide applicability to imines.

Three-component carbon-carbon bond-forming reactions catalyzed by a Br?nsted acid-surfactant-combined catalyst in water

Reactions of aldehydes, amines, and various nucleophiles such as silyl enolates, ketones, Danishefsky's diene, and allyltribuyltin in water were successfully carried out in the presence of p-dodecylbenzenesulfonic acid (DBSA) as a Br?nsted acid-surfactant-combined catalyst.

Organic Photoredox-Catalyzed Synthesis of δ-Fluoromethylated Alcohols and Amines via 1,5-Hydrogen-Transfer Radical Relay

The hydrotrifluoromethylation of benzyl-protected homoallylic alcohol and amine derivatives catalyzed by 2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile (4CzIPN) was developed. This reaction delivered δ-fluoromethylated free alcohols and amines with in situ deprotection of benzyl protecting group under mild irradiation conditions. 4CzIPN was found to be a competent metal-free photoredox catalyst for activating several types of fluoromethylation reagents including CF3SO2Cl, Togni's reagent, and 2-bromo-2,2-difluoroacetate via oxidative quenching and also CF3SO2Na through reductive quenching to allow direct hydrotrifluoromethylation of simple alkenes and Michael acceptors.

Asymmetric Petasis Borono-Mannich Allylation Reactions Catalyzed by Chiral Biphenols

Chiral biphenols catalyze the asymmetric Petasis borono-Mannich allylation of aldehydes and amines through the use of a bench-stable allyldioxaborolane. The reaction proceeds via a two-step, one-pot process and requires 2–8 mole % of 3,3′-Ph2-BINOL as the optimal catalyst. Under microwave heating the reaction affords chiral homoallylic amines in excellent yields (up to 99 %) and high enantioselectivies (er up to 99:1). The catalytic reaction is a true multicomponent condensation reaction whereas both the aldehyde and the amine can possess a wide range of structural and electronic properties. Use of crotyldioxaborolane in the reaction results in stereodivergent products with anti- and syn-diastereomers both in good diastereoselectivities and enantioselectivities from the corresponding E- and Z-borolane stereoisomers.

Amine Functionalization through Sequential Quinone-Catalyzed Oxidation/Nucleophilic Addition

A simple and efficient method for the synthesis of α-branched amines through formal oxidative C–H functionalization is reported. A commercially available quinone organocatalyst is employed to promote the aerobic oxidation of primary amines to the corresponding N-protected imines, which are then trapped in situ with an appropriate nucleophile to give access to versatile functionalized amines in good to excellent yields (70–90 %).

Synthesis of homoallylic amines and acylhydrazides by tin powder-promoted multicomponent one-pot allylation reactions

An efficient process for the synthesis of homoallylic amines and N′-homoallylic hydrazides is developed from the one-pot reaction of carbonyl compounds, amines or N-acylhydrazines, allyllic bromide and tin powder using water as solvent. N-Acylhydrazines are found to be more reactive than amines in these processes. They can react not only with aldehydes but also with ketones to give the corresponding N′-homoallylic hydrazides. Copyright

Sn-mediated one-pot four-component allylation of aldimines

A convenient and facile method for the synthesis of homoallylic amines was disclosed. The one-pot reaction of aldehydes, aromatic amines and allylic bromide with tin powder at room temperature could afford the homoallylic amines in good to excellent yield

Catalytic use of zinc amide for transmetalation with allylboronates: General and efficient catalytic allylation of carbonyl compounds, imines, and hydrazones

The efficient catalytic allylation of ketones, imines, and hydrazones with allylboronates using a catalytic amount of zinc amide is reported. In this reaction, the boron-to-zinc exchange process occurred smoothly to afford the corresponding allylzinc amides, and the desired allylation reactions proceeded in high efficiency (～0.1mol%). A mechanistic study revealed that transmetalation was a rate-determining step in the catalytic cycle, and also that the amide ligand on the zinc center played a key role in preparing reactive allylzinc species. Catalytic asymmetric allylations were also investigated, and high enantioselectivities were obtained using chiral diamine ligands. Copyright

An efficient three-component synthesis of homoallylic amines catalysed by MgI2 etherate

A three-component reaction of aldehydes, amines and allyltributylstannane was efficiently carried out to afford the corresponding homoallylic amine derivatives in the presence of 20 mol% of MgI2 etherate [(MgI 2?(OEt2)n] under mild and neutral reaction conditions in good to excellent yields.

Facile preparation of allylzinc species from allylboronates and zinc amide via a boron-to-zinc exchange process and their reactions with carbonyl compounds, imines and hydrazones

Facile formation of allylzinc species from allylboronate and zinc amide was discovered. The boron-to-zinc exchange process occurred smoothly to afford the corresponding allylzinc amides, which were successfully employed in catalytic allylation reactions with electrophiles. Asymmetric catalysis using a chiral zinc amide is also reported.