131320-85-9

Upstream product

• 124-19-6 nonan-1-al 
• 591-50-4 iodobenzene 
• 111-83-1 1-bromo-octane 
• 100-52-7 benzaldehyde 
• 17049-49-9 octylmagnesium bromide 
• 103687-22-5 ((CH₃)3C₆H₂)2BCHLiC₇H₁₅ 
• 102736-15-2 (1-Chloro-nonyl)-benzene 
• 98-87-3 benzylidene dichloride 
• 3248-78-0 trioctylborane 
• 98875-37-7 2-octyl-1,3,2-benzodioxaborole 
• 98-80-6 phenylboronic acid 
• 111-70-6 n-heptan1ol 
• 98-85-1 1-Phenylethanol 
• 98-86-2 acetophenone 

Downstream Products

• 6008-36-2 1-phenylnonan-1-one 
• 3360-43-8 1-Brom-1-phenyl-nonan 

Relevant academic research and scientific papers

A facile one-pot synthesis of alkylarylcarbinols from α,α-dichloroarylmethanes and trialkylboranes in the presence of magnesium or lithium

α-Chlorobenzylmagnesium chloride or α-chlorobenzyllithium generated from α,α-dichloroarylmethane and magnesium or lithium, reacts in situ with trialkylboranes in THF at room temperature to produce the corresponding alkylarylcarbinols in good yields after oxidation with sodium perborate.

A New Preparation of Diorganozincs from Olefins via a Nickel Catalyzed Hydrozincation

The reaction of olefins with diethylzinc in the presence of catalytic amounts of Ni(acac)2 provides dialkylzincs (neat, 40-50 degC, 2-6 h).These zinc reagents can be trapped by various electrophiles or used for the catalytic asymmetric addition to aldehydes (>85 percent ee).Allylic and homoallylic alcohols are especially good substrates for the reaction.

Design of ionic liquids as a medium for the Grignard reaction

Design of novel phosphonium ionic liquids that are compatible with Grignard reagents have been investigated; several types of phosphonium salts that have an alkyl ether moiety have been synthesized and their capability evaluated as solvents for Grignard reagents. It has been established that even basic aliphatic Grignard reagent-mediated reactions are possible when methoxyethyl(tri-n-butyl)phosphonium bis(trifluoromethanesulfonyl)imide is used as the solvent.

Nickel-catalyzed preparations of functionalized organozincs

The reaction of primary alkyl bromides or chlorides with diethylzinc in the presence of Ni(acac)2 (5 mol %) furnishes the corresponding alkylzinc halides (X = Br, Cl) via a halogen-zinc exchange reaction. The treatment of terminal alkenes with diethylzinc (neat, 25-60°C) in the presence of Ni(acac)2 as a catalyst (1-5 mol %) and 1,5-cyclooctadiene (COD) affords the corresponding dialkylzincs via a hydrozincation reaction. Whereas the conversion for simple alkenes bearing a remote functionality reaches 40 to 63%, the hydrozincation of allylic, homoallylic alcohols and allylic amines proceeds very efficiently (85-95% conversion). All the zinc organometallics obtained react with various electrophiles (allylic halides, enones, acid chlorides, alkynyl halides, ethyl propiolate) after transmetalation with CuCN·2LiCl. In the presence of the chiral catalyst 12, the dialkylzincs prepared add to aldehydes with high enantioselectivity.

Preparation of functionalized dialkylzincs via a boron-zinc exchange. Reactivity and catalytic asymmetric addition to aldehydes

The hydroboration of olefins with Et2BH provides diethyl(alkyl)boranes 2 which readily undergo a boron - zinc exchange with Et2Zn providing a range of polyfunctional primary, secondary, and benzylic diorganozincs. The resulting diorganozincs 3 have been reacted with various electrophiles (allylic halides, acid chlorides, alkylidenemalonates, ethyl propiolate, nitroolefins) in the presence of CuCN·2LiCl with excellent yields. With secondary dialkylzincs prepared from diastereomerically pure diethyl(alkyl)boranes, the boron-zinc exchange occurs with loss of stereochemistry. The asymmetric addition of 3 to aldehydes in the presence of the chiral catalyst 55 furnishes optically active polyfunctional secondary alcohols (50 to over 96% ee).

Ir(NHC)-Catalyzed Synthesis of β-Alkylated Alcohols via Borrowing Hydrogen Strategy: Influence of Bimetallic Structure

Multi N-heterocyclic carbene(NHC)-modified iridium catalysts were employed in the β-alkylation of alcohols; dimerization of primary alcohols (Guerbet reaction), cross-coupling of secondary and primary alcohols, and intramolecular cyclization of alcohols. Mechanistic studies of Guerbet reaction, including kinetic experiments, mass analysis, and density functional theory (DFT) calculation, were employed to explain the fast reaction promoted by bimetallic catalysts, and the dramatic reactivity increase of monometallic catalysts at the late stage of the reaction. (Figure presented.).

C-C coupling formation using nitron complexes

A series of RuII (1), RhIII (2), IrIII (3, 4), IrI (5) and PdII (6-9) complexes of the 'instant carbene' nitron were prepared and characterized by 1H- and 13C-NMR, FT-IR and elemental analysis. The molecular structures of complexes 1-4 and 6 were determined by X-ray diffraction studies. The catalytic activity of the complexes (1-9) was evaluated in alpha(α)-alkylation reactions of ketones with alcohol via the borrowing hydrogen strategy under mild conditions. These complexes were able to perform this catalytic transformation in a short time with low catalyst and base amounts under an air atmosphere. Also, the PdII-nitron complexes (6-9) were applied in the Suzuki-Miyaura C-C coupling reaction and these complexes successfully initiated this reaction in a short time (30 minutes) using the H2O/2-propanol (1.5?:?0.5) solvent system. The DFT calculations revealed that the Pd0/II/0 pathway was more preferable for the mechanism

Manganese-Catalyzed β-Alkylation of Secondary Alcohols with Primary Alcohols under Phosphine-Free Conditions

Manganese(I) complexes bearing a pyridyl-supported pyrazolyl-imidazolyl ligand efficiently catalyzed the direct β-alkylation of secondary alcohols with primary alcohols under phosphine-free conditions. The β-alkylated secondary alcohols were obtained in moderate to good yields with water formed as the byproduct through a borrowing hydrogen pathway. β-Alkylation of cholesterols was also effectively achieved. The present protocol provides a concise atom-economical method for C-C bond formation from primary and secondary alcohols.

Sodium Bromide-Catalyzed Oxidation of Secondary Benzylic Alcohols Using Aqueous Hydrogen Peroxide as Terminal Oxidant

A halide salt, hydroperoxide and AcOH catalyst system was applied to the oxidation of secondary benzylic alcohols. This simple system can be applied to a variety of secondary benzylic alcohols and scaled up for gram-scale preparation. High secondary benzylic alcohol selectivity of the present method is demonstrated in hydroxyketone synthesis. Based on several experimental results, a catalytic cycle for our oxidation is proposed.

A ruthenium catalyst with simple triphenylphosphane for the enantioselective hydrogenation of aromatic ketones

An efficient Ru catalyst constructed from simple and commercially available triphenylphosphane and enantiopure (1S,1′S)-1,1′-biisoindoline (BIDN) was applied to the asymmetric hydrogenation of aromatic ketones. A range of simple aromatic ketones could be hydrogenated with good to excellent enantioselectivities (up to 95% ee). An appropriate enantioselective transition state was proposed to explain the high enantioselectivity obtained with this catalytic system. This study represents the first example to establish a practical Noyori-type catalyst with a simple achiral monophosphane for highly enantioselective hydrogenation. Keep it simple: An efficient Ru catalyst constructed from simple and commercially available triphenylphosphane and enantiopure (1S,1′S)-1,1′-biisoindoline (BIDN) was applied to the asymmetric hydrogenation of aromatic ketones. A range of simple aromatic ketones could be hydrogenated with good to excellent enantioselectivities (up to 95% ee).