6938-51-8

Upstream product

• 93-58-3 benzoic acid methyl ester 
• 4128-31-8 rac-octan-2-ol 
• 591-50-4 iodobenzene 
• 201230-82-2 carbon monoxide 
• 111-71-7 heptanal 
• 95673-88-4 CH₃Cl₂Cr 
• 532-32-1 sodium benzoate 
• 924-80-1 2-octyl mesylate 
• 17265-04-2 cesium benzoate 
• 67810-87-1 2-Octyl benzyl ether 
• 98-88-4 benzoyl chloride 
• 65-85-0 benzoic acid 
• 73377-30-7 N-n-octyl-5,6,8,9-tetrahydro-7-phenyldibenzacridinium trifluoromethanesulfonate 
• 557-35-7 2-bromooctane 

Downstream Products

• 5978-70-1 (R)-Octan-2-ol 

Relevant academic research and scientific papers

Tropolonate salts as acyl-transfer catalysts under thermal and photochemical conditions: Reaction scope and mechanistic insights

Acyl-transfer catalysis is a frequently used tool to promote the formation of carboxylic acid derivatives, which are important synthetic precursors and target compounds in organic synthesis. However, there have been only a few structural motifs known to efficiently catalyze the acyl-transfer reaction. Herein, we introduce a different acyl-transfer catalytic paradigm based on the tropolone framework. We show that tropolonate salts, due to their strong nucleophilicity and photochemical activity, can promote the coupling reaction between alcohols and carboxylic acid anhydrides or chlorides to give products under thermal or blue light photochemical conditions. Kinetic studies and density functional theory calculations suggest interesting mechanistic insights for reactions promoted by this acyl-transfer catalytic system.

Catalytic conversion of ketones to esters: Via C(O)-C bond cleavage under transition-metal free conditions

The catalytic conversion of ketones to esters via C(O)-C bond cleavage under transition-metal free conditions is reported. This catalytic process proceeds under solvent-free conditions and offers an easy operational procedure, broad substrate scope with excellent selectivity, and reaction scalability. This journal is

Asymmetric Magnesium-Catalyzed Hydroboration by Metal-Ligand Cooperative Catalysis

Asymmetric catalysis with readily available, cheap, and non-toxic alkaline earth metal catalysts represents a sustainable alternative to conventional synthesis methodologies. In this context, we describe the development of a first MgII-catalyzed enantioselective hydroboration providing the products with excellent yields and enantioselectivities. NMR spectroscopy studies and DFT calculations provide insights into the reaction mechanism and the origin of the enantioselectivity which can be explained by a metal-ligand cooperative catalysis pathway involving a non-innocent ligand.

Mechanism-Based Enantiodivergence in Manganese Reduction Catalysis: A Chiral Pincer Complex for the Highly Enantioselective Hydroboration of Ketones

A manganese alkyl complex containing a chiral bis(oxazolinyl-methylidene)isoindoline pincer ligand is a precatalyst for a catalytic system of unprecedented activity and selectivity in the enantioselective hydroboration of ketones, thus producing preparatively useful chiral alcohols in excellent yields with up to greater than 99 % ee. It is applicable for both aryl alkyl and dialkyl ketone reduction under mild reaction conditions (TOF >450 h?1 at ?40 °C). The earth-abundant base-metal catalyst operates at very low catalyst loadings (as low as 0.1 mol %) and with a high level of functional-group tolerance. There is evidence for the existence of two distinct mechanistic pathways for manganese-catalyzed hydride transfer and their role for enantiocontrol in the selectivity-determining step is presented.

Broad Scope Synthesis of Ester Precursors of Nonfunctionalized Chiral Alcohols Based on the Asymmetric Hydrogenation of α,β-Dialkyl-, α,β-Diaryl-, and α-Alkyl-β-aryl-vinyl Esters

The catalytic asymmetric hydrogenation of trisubstituted enol esters using Rh catalysts bearing chiral phosphine-phosphite ligands (P-OP) has been studied. Substrates covered comprise α,β-dialkyl, α-alkyl-β-aryl, and α,β-diarylvinyl esters, the corresponding hydrogenation products being suitable precursors to prepare synthetically relevant chiral nonfunctionalized alcohols. A comparison of reactivity indicates that it decreases in the order: α,β-dialkyl > α-alkyl-β-aryl > α,β-diaryl. Based on the highly modular structure of P-OP ligands employed, catalyst screening identified highly enantioselective catalysts for α,β-dialkyl (95-99% ee) and nearly all of α-alkyl-β-aryl substrates (92-98% ee), with the exception of α-cyclohexyl-β-phenylvinyl acetate which exhibited a low enantioselectivity (47% ee). Finally, α,β-diarylvinyl substrates showed somewhat lower enantioselectivities (79-92% ee). In addition, some of the catalysts provided a high enantioselectivity in the hydrogenation of E/Z mixtures (ca. Z/E = 75:25) of α,β-dialkylvinyl substrates, while a dramatic decrease on enantioselectivity was observed in the case of α-methyl-β-anisylvinyl acetate (Z/E = 58:42). Complementary deuteration reactions are in accord with a highly enantioselective hydrogenation for both olefin isomers in the case of α,β-dialkylvinyl esters. In contrast, deuteration shows a complex behavior for α-methyl-β-anisylvinyl acetate derived from the participation of the E isomer in the reaction.

Sodium cyanide-promoted copper-catalysed aerobic oxidative synthesis of esters from aldehydes

A simple and efficient copper-catalysed procedure for oxidative esterification of aldehydes with alcohols and phenols mediated by sodium cyanide, using air as a clean oxidant, is described. A variety of aromatic aldehydes and structurally different alcohols and phenols reacted efficiently, and the product esters were obtained in good to excellent yields under normal atmospheric and solvent-free conditions.

METHOD OF CONVERTING ALCOHOL TO HALIDE

The present invention relates to a method of converting an alcohol into a corresponding halide. This method comprises reacting the alcohol with an optionally substituted aromatic carboxylic acid halide in presence of an N-substituted formamide to replace a hydroxyl group of the alcohol by a halogen atom. The present invention also relates to a method of converting an alcohol into a corresponding substitution product. The second method comprises: (a) performing the method of the invention of converting an alcohol into the corresponding halide; and (b) reacting the corresponding halide with a nucleophile to convert the halide into the nucleophilic substitution product.

Majority-Rules-Type Helical Poly(quinoxaline-2,3-diyl)s as Highly Efficient Chirality-Amplification Systems for Asymmetric Catalysis

A highly efficient majority-rules effect of poly(quinoxaline-2,3-diyl)s (PQXs) bearing 2-butoxymethyl chiral side chains at the 6- and 7-positions was established and attributed to large ΔGh values (0.22-0.41 kJmol-1), which are defined as the energy difference between P- and M-helical conformations per chiral unit. A PQX copolymer prepared from a monomer derived from (R)-2-octanol (23% ee) and a monomer bearing a PPh2 group adopted a single-handed helical structure (>99%) and could be used as a highly enantioselective chiral ligand in palladium-catalyzed asymmetric reactions (products formed with up to 94% ee), in which the enantioselectivity could be switched by solvent-dependent inversion of the helical PQX backbone. Bowing to the majority: Poly(quinoxaline-2,3-diyl) containing PPh2 groups and chiral side chains derived from (R)-2-octanol with 23% ee exhibited a single-handed-helical conformation and served as a highly enantioselective chiral ligand in palladium-catalyzed reactions (see scheme; se=screw-sense excess). The chirality of the polymer could be switched by a solvent effect to enable the synthesis of the enantiomeric products.

Ester manufacturing method (by machine translation)

PROBLEM TO BE SOLVED: To produce an ester compound by transesterification using an inexpensive and low toxic inorganic compound. SOLUTION: Transesterification of an ester compound and an alcohol compound is carried out under the presence of lanthanum nitrate (for example, lanthanum nitrate hexahydrate) and a phosphine compound (for example, tri-n-octylphosphine), thereby obtaining the ester product. For example, transesterification of dimethyl carbonate and benzyl alcohol is carried out under the presence of 1 mol% of lanthanum nitrate hexahydrate, and 2 mol% of tri-n-octylphosphine, thereby obtaining benzyl methylcarbonate at a yield of >99%. COPYRIGHT: (C)2012,JPO&INPIT

Co-oxidation of octane and benzaldehyde using molecular oxygen with Au-Pd/carbon prepared by sol-immobilisation

The selective oxidation of linear alkanes with molecular oxygen under mild conditions remains a challenging topic in the field of catalysis. In this study we investigate the co-oxidation of C-H bonds in substrates with different relative reactivities, the aim being to couple the oxidised products in situ to form the corresponding esters. Initial attempts were made to co-oxidise octane with toluene to form octyl benzoate using Au-Pd catalysts. During the study the oxidation of octane in the presence of benzaldehyde, an oxidation product of toluene, was also investigated in order to demonstrate the potential feasibility of the reaction. This work summarises our attempts to show whether a co-oxidation system could be an effective way to oxidise linear alkanes.