115833-91-5

Upstream product

• 39910-98-0 4-morpholinoacetophenone 
• 403-42-9 1-(4-fluorophenyl)ethanone 

Downstream Products

• 1019780-37-0 C₁₅H₁₉N₃O 
• 2524-67-6 4-morpholino-4-yl-phenylamine 
• 1344921-45-4 (S)-1-[4-(morpholin-4-yl)phenyl]ethanol 

Relevant academic research and scientific papers

Selective Carbon-Carbon Bond Amination with Redox-Active Aminating Reagents: A Direct Approach to Anilines?

Amines are among the most fundamental motifs in chemical synthesis, and the introduction of amine building blocks via selective C—C bond cleavage allows the construction of nitrogen compounds from simple hydrocarbons through direct skeleton modification. Herein, we report a novel method for the preparation of anilines from alkylarenes via Schmidt-type rearrangement using redox-active amination reagents, which are easily prepared from hydroxylamine. Primary amines and secondary amines were prepared from corresponding alkylarenes or benzyl alcohols under mild conditions. Good compatibility and valuable applications of the transformation were also displayed.

RETRACTED ARTICLE: The Manganese(I)-Catalyzed Asymmetric Transfer Hydrogenation of Ketones: Disclosing the Macrocylic Privilege

The bis(carbonyl) manganese(I) complex [Mn(CO)2(1)]Br (2) with a chiral (NH)2P2 macrocyclic ligand (1) catalyzes the asymmetric transfer hydrogenation of polar double bonds with 2-propanol as the hydrogen source. Ketones (43 substrates) are reduced to alcohols in high yields (up to >99 %) and with excellent enantioselectivities (90–99 % ee). A stereochemical model based on attractive CH–π interactions is proposed.

Silver-Catalyzed Hydrogenation of Ketones under Mild Conditions

The silver-catalyzed hydrogenation of ketones using H2 as hydrogen source is reported. Silver nanoparticles are generated from simple silver (I) salts and operate at 25 °C under 20 bar of hydrogen pressure. Various aliphatic and aromatic ketones, including natural products were reduced into the corresponding alcohols in high yields. This silver catalyst allows for the selective hydrogenation of ketones in the presence of other functional groups. (Figure presented.).

Base-Mediated Meerwein-Ponndorf-Verley Reduction of Aromatic and Heterocyclic Ketones

An experimental protocol to achieve the Meerwein-Ponndorf-Verley (MPV) reduction of ketones under mildly basic conditions is reported. The transformation is tolerant of a range of ketone substrates, including O- and S-containing heterocycles, is scalable, and shows potential to be used as a platform to access enantioenriched products. These studies provide a general method for achieving the reduction of ketones under mildly basic conditions and offer an alternative protocol to more well-known Al-based MPV reduction conditions.

Hydrogenation of Carbonyl Derivatives with a Well-Defined Rhenium Precatalyst

The first efficient and general rhenium-catalyzed hydrogenation of carbonyl derivatives was developed. The key to the success of the reaction was the use of a well-defined rhenium complex bearing a tridentate diphosphinoamino ligand as the catalyst (0.5 mol %) at 70 °C in the presence of H2 (30 bar). The mechanism of the reaction was investigated by DFT(PBE0-D3) calculations.

Transfer Hydrogenation of Carbonyl Derivatives Catalyzed by an Inexpensive Phosphine-Free Manganese Precatalyst

A very simple and inexpensive catalytic system based on abundant manganese as transition metal and on an inexpensive phosphine-free bidendate ligand, 2-(aminomethyl)pyridine, has been developed for the reduction of a large variety of carbonyl derivatives with 2-propanol as hydrogen donor. Remarkably, the reaction proceeds at room temperature with low catalyst loading (down to 0.1 mol %) and exhibits a good tolerance toward functional groups. High TON (2000) and TOF (3600 h-1) were obtained.

Asymmetric Reduction of Electron-Rich Ketones with Tethered Ru(II)/TsDPEN Catalysts Using Formic Acid/Triethylamine or Aqueous Sodium Formate

The asymmetric transfer hydrogenation (ATH) of ketones under aqueous conditions using tethered Ru(II)/6-arene/diamine catalysts is described, as is the ATH of electron-rich substrates containing amine and methoxy groups on the aromatic rings. Although such substrates are traditionally challenging ones for ATH, the tethered catalysts work very efficiently. In the case of amino-substituted ketones, aqueous conditions give excellent results; however, for methoxy-substituted substrates, the more established formic acid/triethylamine system gives superior results.

Ruthenium-catalyzed transfer hydrogenation of amino- and amido-substituted acetophenones

The ruthenium-catalyzed transfer hydrogenation of electron-rich amino-substituted acetophenones is reported. Variation of the reductant, ligands, base, and solvent allowed reaction optimization. A key discovery was the use of 1,4-butanediol as an irreversible reducing agent, which significantly improved the conversion. A range of amino- and amido-substituted aryl ketones were explored, and they all gave the corresponding alcohols in good yield, which demonstrates the wider applicability of this process. The ruthenium-catalyzed reduction of electron-rich amino-substituted acetophenones with 1,4-butanediol as an irreversible reducing agent is reported. Optimization of the conditions and variation of the amino substituent are explored as is the use of amido- and sulfonamidoacetophenones with varying results. Copyright

Iron dihydride complex as the pre-catalyst for efficient hydrosilylation of aldehydes and ketones under visible light activation

A general and efficient hydrosilylation of aldehydes and ketones into the corresponding alcohols using the well-defined bis(diphenylphosphinoethane)iron dihydride complex as the pre-catalyst is reported using polymethylhydrosiloxane (PMHS) as the reducing silylating agent and sodium tetraethoxyborate [NaB(OEt)4] as a co-catalyst under visible light irradiation. The low catalyst loadings (0.1-1 mol%), the amount of economical hydride source, PMHS and the unconventional way of activation of the pre-catalyst make this new approach attractive.