106560-85-4

Upstream product

• 6048-82-4 decanophenone 
• 764-93-2 1-decyne 
• 100-58-3 phenylmagnesium bromide 
• 111-87-5 octanol 
• 98-85-1 1-Phenylethanol 
• 98-86-2 acetophenone 
• 5123-13-7 5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane 
• 872-05-9 1-Decene 
• 1334446-77-3 ⁽¹⁸⁾O-n-decanal dimethyl acetal 
• 112-31-2 caprinaldehyde 
• 934-56-5 trimethyl(phenyl)stannane 
• 110-42-9 Methyl decanoate 
• 39691-62-8 nonylmagnesium bromide 
• 100-52-7 benzaldehyde 

Downstream Products

• 1975-78-6 n-decanenitrile 
• 103-84-4 Acetanilid 
• 1795-16-0 decylcyclohexane 
• 120783-80-4 1-phenyl-1-phenylacetamido-decane 
• 33206-62-1 dec-1-en-1-ylbenzene 
• 120783-79-1 1-acetamido-1-phenyl-decane 

Relevant academic research and scientific papers

Reaction of I2 with α-boraalkylmagnesium bromide: A new synthesis of mixed alkyl secondary alcohols

1,1-Diborylalkanes, prepared through hydroboration of 1-alkynes using BH3:N(C2H5)2Ph complex, on reaction with Grignard reagent followed by I2/NaOH treatment and H2O2/OH- oxidation give the corresponding mixed alkyl secondary alcohols.

Pyridine is an organocatalyst for the reductive ozonolysis of alkenes

Whereas the cleavage of alkenes by ozone typically generates peroxide intermediates that must be decomposed in an accompanying step, ozonolysis in the presence of pyridine directly generates ketones or aldehydes through a process that neither consumes pyridine nor generates any detectable peroxides. The reaction is hypothesized to involve nucleophile-promoted fragmentation of carbonyl oxides via formation of zwitterionic peroxyacetals.

Titanocene-catalysed, selective reduction of ketones in aqueous media. A safe, mild, inexpensive procedure for the synthesis of secondary alcohols via radical chemistry

We report here a novel procedure for the reduction of ketones to secondary alcohols using catalytic quantities of commercially available Cp2TiCl2, inexpensive Zn dust and water as proton source. Mechanistically the reaction presumably proceeds via titanoxy radicals. In practice this reduction process has significant advantages: it shows an interesting selectivity pattern, takes place under mild conditions using safe, cheap reagents and does not require anhydrous solvents. The proton-donor activity of water under these conditions avoids the use of the frequently poisonous hydrogen-atom donors generally required to reduce free radicals. This procedure is also highly convenient for synthesising deuterium-labelled alcohols employing relatively inexpensive D2O as deuterium source.

Reductive Arylation of Amides via a Nickel-Catalyzed Suzuki–Miyaura-Coupling and Transfer-Hydrogenation Cascade

We report a means to achieve the addition of two disparate nucleophiles to the amide carbonyl carbon in a single operational step. Our method takes advantage of non-precious-metal catalysis and allows for the facile conversion of amides to chiral alcohols via a one-pot Suzuki–Miyaura cross-coupling/transfer-hydrogenation process. This study is anticipated to promote the development of new transformations that allow for the conversion of carboxylic acid derivatives to functional groups bearing stereogenic centers via cascade processes.

Selective C-alkylation Between Alcohols Catalyzed by N-Heterocyclic Carbene Molybdenum

The first implementation of a molybdenum complex with an easily accessible bis-N-heterocyclic carbene ligand to catalyze β-alkylation of secondary alcohols via borrowing-hydrogen (BH) strategy using alcohols as alkylating agents is reported. Remarkably high activity, excellent selectivity, and broad substrate scope compatibility with advantages of catalyst usage low to 0.5 mol%, a catalytic amount of NaOH as the base, and H2O as the by-product are demonstrated in this green and step-economical protocol. Mechanistic studies indicate a plausible outer-sphere mechanism in which the alcohol dehydrogenation is the rate-determining step.

Switchable β-alkylation of secondary alcohols with primary alcohols by a well-defined cobalt catalyst

β-alkylation of secondary alcohols with primary alcohols to selectively generate alcohols by a well-defined Co catalyst is presented. Remarkably, a low catalyst loading of 0.7 mol % can be employed for the reaction. More significantly, this study represents the first Co-catalyzed switchable alcohol/ketone synthesis by simply manipulating the reaction parameters. In addition, the transformation is environmentally friendly, with water as the only byproduct.

Pincer-Nickel Catalyzed Selective Guerbet-Type Reactions

We report here the synthesis and characterization of a series of NNN pincer-nickel complexes of the type (R2NNN)NiCl2(CH3CN) (R = iPr, tBu, Cy, Ph, and p-F-C6H4) based on bis(imino)pyridine ligands. In solution, these complexes are found to be equilibrium mixtures containing one and two pincer ligands, respectively. While the crystal structure of the former was reported by us recently for R = iPr, we report the crystal structure of the latter in this study for R = p-F-C6H4. The considered NNN pincer-Ni complexes have been successfully employed to accomplish the catalytic β-alkylation of several secondary alcohols with a variety of benzyl alcohols at 140 °C with high yields and unprecedented turnovers. A maximum of 92% yield of the β-alkylated product at 18 ?400 TON was obtained in the reaction of benzyl alcohol with 1-(4-(trifluoromethyl)phenyl)ethane-1-ol in the presence of 0.005 mol % of (Ph2NNN)NiCl2(CH3CN) and 5 mol % of NaOtBu at 140 °C after 24 h. The reaction exhibits zero-order dependence of rate on catalyst concentration and first-order dependence on the concentration of base, benzyl alcohol, and 1-phenyl ethanol which points to the base-mediated aldol condensation as the rate-determining step. Most of the intermediates involved in catalysis have been identified by HRMS. To the best of our knowledge, this is the first report on a pincer-Ni catalyzed β-alkylation of alcohols and, hitherto, such unprecedented turnovers have not been reported with a homogeneous molecular nickel-based catalyst.

Phosphine-free pincer-ruthenium catalyzed biofuel production: High rates, yields and turnovers of solventless alcohol alkylation

Phosphine-free pincer-ruthenium carbonyl complexes based on bis(imino)pyridine and 2,6-bis(benzimidazole-2-yl) pyridine ligands have been synthesized. For the β-alkylation of 1-phenyl ethanol with benzyl alcohol at 140 °C under solvent-free conditions, (Cy2NNN)RuCl2(CO) (0.00025 mol%) in combination with NaOH (2.5 mol%) was highly efficient (ca. 93% yield, 372?000 TON at 12?000 TO h-1). These are the highest reported values hitherto for a ruthenium based catalyst. The β-alkylation of various alcohol combinations was accomplished with ease which culminated to give 380?000 TON at 19?000 TO h-1 for the β-alkylation of 1-phenyl ethanol with 3-methoxy benzyl alcohol. DFT studies were complementary to mechanistic studies and indicate the β-hydride elimination step involving the extrusion of acetophenone to be the overall RDS. While the hydrogenation step is favored for the formation of α-alkylated ketone, the alcoholysis step is preferred for the formation of β-alkylated alcohol. The studies were extended for the upgradation of ethanol to biofuels. Among the pincer-ruthenium complexes based on bis(imino)pyridine, (Cy2NNN)RuCl2(CO) provided high productivity (335 TON at 170 TO h-1). Sterically more open pincer-ruthenium complexes such as (Bim2NNN)RuCl2(CO) based on the 2,6-bis(benzimidazole-2-yl) pyridine ligand demonstrated better reactivity and gave not only good ethanol conversion (ca. 58%) but also high turnovers (ca. 2100) with a good rate (ca. 710 TO h-1). Kinetic studies indicate first order dependence on concentration of both the catalyst and ethanol. Phosphine-free catalytic systems operating with unprecedented activity at a very low base loading to couple lower alcohols to higher alcohols of fuel and pharmaceutical importance are the salient features of this report. This journal is

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

Iridium(I)-Catalyzed C-C and C-N Bond Formation Reactions via the Borrowing Hydrogen Strategy

Iridium(I) complexes having an imidazol-2-ylidene ligand with benzylic wingtips efficiently catalyzed the β-alkylation of secondary alcohols with primary alcohols and acceptorless dehydrogenative cyclization of 2-aminobenzyl alcohol with ketones through a borrowing hydrogen pathway. The β-alkylated alcohols, including cholesterol derivatives, and substituted quinolines were obtained in good yields by using a minute amount of the catalyst with a catalytic amount of NaOH or KOH under the air atmosphere, liberating water (and H2 in the case of quinoline synthesis) as the sole byproduct. Notably, this system demonstrated turnover numbers of 940 000 (for β-alkylation of secondary alcohols with primary alcohols by using down to 0.0001 mol % = 1 ppm of the catalyst) and 9200 (acceptorless dehydrogenative cyclization of 2-aminobenzyl alcohol with ketones).