65559-74-2

Upstream product

• 60699-32-3 (E)-3,7-dimethylocta-2,6-dien-1-yl diethyl phosphate 
• 60699-28-7 dimethylaluminum anilide 
• 62-53-3 aniline 
• 5389-87-7 1-chloro-3,7-dimethylocta-2,6-diene 
• 141-27-5 3,7-dimethyl-2,6-octadienal 
• 6246-48-6 geranylamine 
• 98-80-6 phenylboronic acid 
• 105-87-3 3,7-dimethyl-2E,6-octadien-1-yl acetate 
• 106-24-1 Geraniol 
• 624-15-7 geraniol 
• 1440356-34-2 C₂₂H₂₈N₂ 
• 5392-40-5 (E/Z)-3,7-dimethyl-2,6-octadienal 
• 78-70-6 3,7-dimethylocta-1,6-dien-3-ol 

Relevant academic research and scientific papers

BF3·Et2O as a metal-free catalyst for direct reductive amination of aldehydes with amines using formic acid as a reductant

A versatile metal- and base-free direct reductive amination of aldehydes with amines using formic acid as a reductant under the catalysis of inexpensive BF3·Et2O has been developed. A wide range of primary and secondary amines and diversely substituted aldehydes are compatible with this transformation, allowing facile access to various secondary and tertiary amines in high yields with wide functional group tolerance. Moreover, the method is convenient for the late-stage functionalization of bioactive compounds and preparation of commercialized drug molecules and biologically relevant N-heterocycles. The procedure has the advantages of simple operation and workup and easy scale-up, and does not require dry conditions, an inert atmosphere or a water scavenger. Mechanistic studies reveal the involvement of imine activation by BF3and hydride transfer from formic acid.

Synthesis and biological activities of (E)-β-farnesene analogues containing 1,2,3-thiadiazole

In order to discover novel compounds with high-activity to control aphid, a series of novel (E)-β-farnesene analogues containing 1,2,3-thiadiazole were designed and synthesized, and their structures were confirmed by IR,1H NMR,13C NMR, and HRMS (ESI). The stability of representative compounds was studied by HPLC and1H NMR techniques. Repellent activity results indicated that compounds 8h and 8j displayed 60.3% and 62.0% repellent rates, respectively. The aphicidal bioassay results showed that most analogues exhibited considerable aphicidal activity against Myzus persicae. Especially, analogues 8l, 8s and 8t exhibited high activity with LC50values of 33.4?μg/mL, 50.2?μg/mL and 61.8?μg/mL, respectively, which were higher than the lead compound (E)-β-farnesene, but lower than commercial insecticide pymetrozine with a LC50of 7.1?μg/mL.

Hydrogen-bond-assisted activation of allylic alcohols for palladium-catalyzed coupling reactions

We report direct activation of allylic alcohols using a hydrogen-bond-assisted palladium catalyst and use this for alkylation and amination reactions. The novel catalyst comprises a palladium complex based on a functionalized monodentate phosphoramidite ligand in combination with urea additives and affords linear alkylated and aminated allylic products selectively. Detailed kinetic analysis show that oxidative addition of the allyl alcohol is the rate-determining step, which is facilitated by hydrogen bonds between the alcohol, the ligand functional group, and the additional urea additive. Hydrogen Bond Rule(s): Direct activation of allylic alcohols and subsequent alkylation and amination reactions are reported. The new catalyst is based on functionalized palladium and phosphoramidite ligands to allow hydrogen bond-assisted activation. Kinetic data are in line with this mechanism as the oxidative addition is the rate-determining step.

α-Selective allylation of azo compounds using allylic barium reagents

The addition of allylic barium reagents to azo compounds was achieved with high α-regioselectivity. The double-bond geometry of allylic barium reagents was retained throughout the reaction at -78 °C and E- or Z-enriched allylic hydrazines were selectively

Iron/amino acid catalyzed direct N-alkylation of amines with alcohols

(Chemical Equation Presented) Ironing it out: The straightforward N-alkylation using alcohols and iron/amino acid catalysis is described (see scheme). The reaction does not proceed by the conventional "borrowing hydrogen" mechanism, but appears to involve a substitution pathway (S N) at the sp3 carbon atom bearing the hydroxy group of the alcohol. Developing a catalyst that is effective at a near neutral pH was key to the successful N-alkylation.

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.

Diphosphines of dppf-type incorporating electron-withdrawing furyl moieties substantially improve the palladium-catalysed amination of allyl acetates

Highly active Pd/diphosphine catalytic systems incorporating new, air-stable ferrocenyl-furylphosphines allow nucleophilic allylic amination at room temperature with unprecedented turnover frequencies. For instance, in the presence of 0.01 mol % catalyst the coupling of aniline to allyl acetate occurs at a TOF of more than 10,000 h-1; even the addition of the less nucleophile morpholine to allyl acetate is observed with a TOF of 4250 h -1. The amination of the sterically demanding geranyl acetate, a monoterpene derivative of interest in the flavour industry, at low catalyst loadings demonstrates the scope of this methodology, which provides in addition noticeable advantages in terms of economical (resource- and energy-saving) and sustainable chemistry (high selectivity, no additive, low metal content, and thus easier purification).

Ligand- and Base-Free Copper(II)-Catalyzed C-N Bond Formation: Cross-Coupling Reactions of Organoboron Compounds with Aliphatic Amines and Anilines

(Equation presented) A ligandless and base-free Cu-catalyzed protocol for the cross-coupling of arylboronic acids and potassium aryltrifluoroborate salts with primary and secondary aliphatic amines and anilines is described. The process utilizes catalytic copper(II) acetate monohydrate and 4 A molecular sieves in dichloromethane at slightly elevated temperatures under an atmosphere of oxygen. A broad range of functional groups are tolerated on both of the cross-coupling partners.