130517-97-4

Upstream product

• 100-46-9 benzylamine 
• 2043-61-0 cyclohexanecarbaldehyde 
• 100-49-2 cyclohexylmethyl alcohol 
• 35665-26-0 N-benzylcyclohexanecarboxamide 
• 622-79-7 benzyl azide 
• 183864-20-2 N-[(2-bromophenyl)methylidene]-N-(2-propenyl)amine 
• 6630-33-7 ortho-bromobenzaldehyde 
• 1072-95-3 cyclohexylmethyl chloride 

Downstream Products

• 141120-51-6 N-benzyl-2,3-dihydro-2-(c-hexyl)-4-pyridone 
• 141120-51-6 N-benzyl-2,3-dihydro-2-(c-hexyl)-4-pyridone 
• 82524-63-8 N-Benzyl-N-cyclohexylidenemethyl-formamide 
• 93965-53-8 benzyl(1-cyclohexylbut-3-enyl)amine 
• 203244-87-5 N-benzyl-2,2,2-trichloro-N-cyclohexylidenemethyl-acetamide 
• 347406-43-3 N-benzyl-2-bromo-N-(cyclohexylidenemethyl)-2-methylpropionamide 
• 219680-01-0 (S)-N-benzyl-1-cyclohexylbut-3-en-1-amine 
• 141120-52-7 N-benzyl-2,3-dihydro-2-(c-hexyl)-5-methyl-4-pyridone 
• 141120-52-7 N-benzyl-2,3-dihydro-2-(c-hexyl)-5-methyl-4-pyridone 
• 599171-59-2 2-(benzylamino)-2-cyclohexylacetonitrile 
• 93965-54-9 (1RS,2SR)-N-phenylmethyl-1-cyclohexyl-2-methyl-3-buten-1-amine 
• 93965-54-9 (1RS,2RS)-N-phenylmethyl-1-cyclohexyl-2-methyl-3-buten-1-amine 

Relevant academic research and scientific papers

A stereoselective synthesis of alkynylaziridines

Reactions between allenylzinc carbenoid 1 and various imines were examined; trans-substituted alkynylaziridines were produced with excellent diastereoselectivity. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

Synthesis of a Triphenylphosphine Reagent on Non-cross-linked Polystyrene Support: Application to the Staudinger/Aza-Wittig Reaction

formula presented A new triphenylphosphine reagent linked to a linear polystyrene was synthesized. The reactivity of this phosphine-bound polymer is superior to that of the phosphine bound to cross-linked polystyrene. The polymer reacted very rapidly with azides to generate iminophosphoranes which could then react with aldehydes to generate imines in good yields and high purities.

Trimethyl Borate-Catalyzed, Solvent-Free Reductive Amination

Solvent-free reductive amination of aldehydes and ketones with aliphatic and aromatic amines in high-to-excellent yields has been achieved with sub-stoichiometric trimethyl borate as promoter and ammonia borane as reductant.

Enantioselective Reductive Cyanation and Phosphonylation of Secondary Amides by Iridium and Chiral Thiourea Sequential Catalysis

The combination of transition-metal catalysis and organocatalysis increasingly offers chemists opportunities to realize diverse unprecedented chemical transformations. By combining iridium with chiral thiourea catalysis, direct enantioselective reductive cyanation and phosphonylation of secondary amides have been accomplished for the first time for the synthesis of enantioenriched chiral α-aminonitriles and α-aminophosphonates. The protocol is highly efficient and enantioselective, providing a novel route to the synthesis of optically active α-functionalized amines from the simple, readily available feedstocks. In addition, the reactions are scalable and the thiourea catalyst can be recycled and reused.

Au nanoparticle-immobilized L-cysteine-paired porous ionic copolymer as an efficient catalyst for additive-free oxidative coupling of alcohols and amines

Herein, an L-cysteine-paired ionic copolymer (DVB-[MimLcy]n) with mesoporosity was prepared by free radical copolymerization of divinylbenzene (DVB) and imidazolium ionic liquids (ILs), followed by anion-exchange with L-cysteine. Because of the rich functional groups of –NH2, –SH, and –COO– and the porous framework, the DVB-[MimLcy]3 was revealed to be an ideal stabilizer for metal nanoparticles (NPs). Highly uniform dispersed small Au NPs (2–3 nm) immobilized on DVB-[MimLcy]3 (Aua/DVB-[MimLcy]3) can act as an efficient heterogeneous catalyst for additive-free synthesis of imines through coupling of a broad range of alcohols and organic amines and can be easily recovered and steadily reused several times.

Activation of primary amines by copper(i)-based lewis acid promoters in the solventless synthesis of secondary propargylamines

Primary amines are activated by copper(I)-based Lewis acid promoters in an A 3 -coupling one-pot solventless reaction with aldehydes and phenylacetylene for the synthesis of secondary propargylamines. The reaction is promoted by a CuSO 4 /NaI system, a practical precursor of the in situ generated effective CuI/I 2 system, that worked well, but only in a restricted number of examples. Substitution of I 2 with CeCl 3 ·7H 2 O in a one-pot two-step reaction provided good yields and a wider applicability, with the added value given by a safer procedure.

Selective aerobic oxidation of halides and amines with an inorganic-ligand supported zinc catalyst

A practical, efficient and environmentally benign catalytic protocol for the oxidative cross-coupling reaction of halides with amines, oxidative self-coupling of amines and oxidation of halides was developed with inorganic-ligand supported ZnPOM (NH4)4[ZnMo6O18(OH)6] using molecular oxygen. This method mainly utilizes an inorganic polymolybdate ligand to support the Zn2+ ion, avoiding the use of complicated organic ligands.

Visible-Light-Driven Photocatalytic Oxidation of Organic Chlorides Using Air and an Inorganic-Ligand Supported Nickel-Catalyst Without Photosensitizers

Engineering photoredox-triggered chemical transformation via visible light has been an emerging area in organic synthesis. However, most of the well-established photocatalysts are based upon either transition metal complexes involved with noble metals and organic ligands or photosensitive organic dyes, the development of pure inorganic molecular photocatalysts that could provide better stability and durability is greatly retarded. Herein we discover that the Anderson polyoxometalate (POM) Na4[NiMo6O18(OH)6] (1), which consists of pure inorganic framework built from a central NiII core supported by six MoVIO6 inorganic scaffold/ligands, can be used as a powerful photocatalyst. Upon irradiation with visible light (>400 nm), the compound can catalyze, in high efficiency, a wide range of reactions, including the oxidative cross-coupling reaction of chlorides with amines, as well as oxidation of chlorides using molecular oxygen, affording various imines, aldehydes, and ketones, respectively in high selectivity and good yields. Owing to the robust inorganic framework, this catalyst exhibits excellent stability during the catalysis and reusability with little loss of the catalytic activity, thus providing an alternative without use of complicated organic ligands and expensive noble metal-based photosensitizers.

One-Pot Reductive Allylation of Amides by Using a Combination of Titanium Hydride and an Allylzinc Reagent: Application to a Total Synthesis of (-)-Castoramine

A one-pot direct reductive allylation protocol has been developed for the synthesis of secondary amines by using titanium hydride and an allylzinc reagent. This protocol is applicable to a broad range of substrates, including acyclic amides, benzamides, α,β-unsaturated amides, and lactams. The stereochemical outcome obtained from the reaction with crotylzinc reagent suggested that the allylation reaction proceeds through a six-membered cyclic transition state. A total synthesis of (-)-castoramine was accomplished by following this protocol for the highly stereoselective construction of contiguous stereocenters.

Transition-Metal-Controlled Inorganic Ligand-Supported Non-Precious Metal Catalysts for the Aerobic Oxidation of Amines to Imines

Most state-of-art transition-metal catalysts usually require organic ligands, which are essential for controlling the reactivity and selectivity of reactions catalyzed by transition metals. However, organic ligands often suffer from severe problems including cost, toxicity, air/moisture sensitivity, and being commercially unavailable. Herein, we show a simple, mild, and efficient aerobic oxidation procedure of amines using inorganic ligand-supported non-precious metal catalysts 1, (NH4)n[MMo6O18(OH)6] (M=Cu2+; Fe3+; Co3+; Ni2+; Zn2+, n=3 or 4), synthesized by a simple one-step method in water at 100 °C, demonstrating that the catalytic activity and selectivity can be significantly improved by changing the central metal atom. In the presence of these catalysts, the catalytic oxidation of primary and secondary amines, as well as the coupling of alcohols and amines, can smoothly proceed to afford various imines with O2 (1 atm) as the sole oxidant. In particular, the catalysts 1 have transition-metal ion core, and the planar arrangement of the six MoVI centers at their highest oxidation states around the central heterometal can greatly enhance the Lewis acidity of catalytically active sites, and also enable the electrons in the center to delocalize onto the six edge-sharing MO6 units, in the same way as ligands in traditional organometallic complexes. The versatility of this methodology maybe opens a path to catalytic oxidation through inorganic ligand-coordinated metal catalysis.