13163-64-9

Upstream product

• 3580-38-9 2-Benzoylcyclohexanone 
• 108-22-5 Isopropenyl acetate 
• 98-88-4 benzoyl chloride 
• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 
• 108-94-1 cyclohexanone 
• 614-45-9 tert-Butyl peroxybenzoate 
• 110-83-8 cyclohexene 
• 93-97-0 benzoic acid anhydride 
• 455-32-3 benzoyl fluoride 
• 65-85-0 benzoic acid 
• 4891-38-7 phenylpropynoic acid methyl ester 

Downstream Products

• 62183-31-7 7-oxabicyclo<4.1.0>hept-1-yl benzoate 
• 25115-73-5 2-(4-chlorophenyl)cyclohexanone 
• 66049-39-6 3-oxo-1-cyclohexen-1-yl benzoate 
• 3580-38-9 2-Benzoylcyclohexanone 
• 216099-51-3 (1R,2R)-1-(benzoyloxy)-1,2-epoxycyclohexane 
• 38268-02-9 benzoic acid ; tripropyl tin-benzoate 

Relevant academic research and scientific papers

Three-Component Coupling of Acyl Fluorides, Silyl Enol Ethers, and Alkynes by P(III)/P(V) Catalysis

We report herein on the phosphine-catalyzed hydrovinylation reaction by three-component coupling of acyl fluorides, silyl enol ethers, and alkynoates. The key to the success of the reaction is the formal transmetalation between pentacoordinate P(V) species (i.e., fluorophosphorane) and a silyl enol ether, which allows for C-C bond formation between the polarity-mismatched sites. The bond formation that cannot be attained even by transition metal catalysis is accomplished by a P(III)/P(V) manifold.

Normal Alpha Olefin Synthesis Using Dehydroformylation or Dehydroxymethylation

The present invention discloses processes for producing normal alpha olefins, such as 1-hexene, 1-octene, 1-decene, and 1-dodecene in a multistep synthesis scheme from another normal alpha olefin. Also disclosed are reactions for converting aldehydes, primary alcohols, and terminal vicinal diols into normal alpha olefins.

Process for Production of Carboxylic Acid Ester or Ether Compound

Disclosed is a process for production of a carboxylic acid ester from a carboxylic acid and an olefin or production of an ether compound from an alcohol and an olefin at low cost and with high yield in an industrially advantageous manner. The process comprises the step of reacting a carboxylic acid with an olefin to yield a corresponding carboxylic acid ester or reacting an alcohol with an olefin to yield a corresponding ether compound. In the process, a catalyst comprising a combination of (i) at least one metal compound selected from an iron compound, a cobalt compound and a nickel compound and (ii) an acidic compound is used.

DMAP-organocatalyzed O-silyl-O-(or C-)-benzoyl interconversions by means of benzoyl fluoride

A mild and efficient transprotection of alcohols from silyl ethers 1a-f to benzoates 2a-f is reported in fair to good yields (50-98%). This silyl-acyl exchange reaction proceeds readily in acetonitrile at room temperature in the presence of benzoyl fluoride and DMAP as an acyl transfer catalyst. A two-step 'one-pot' DMAP-catalyzed silylcyanation-transprotection sequence which gives the corresponding O-benzoyl cyanohydrines 2g-l in high yields (72-98%) from various benzaldehyde and ketone derivatives is also reported. This original organocatalytic acyl transfer process was also found to be effective in the O-benzoylation of trimethysilyl enolates 1m-o, providing enol esters 2m-o. Lastly, the potential of this strategy is also illustrated by a DMAP-mediated Claisen condensation between ketene silyl acetals 1p-r and benzoyl fluoride. Georg Thieme Verlag Stuttgart.

Enantioselective synthesis and stereoselective rearrangements of enol ester epoxides

Enol esters can be epoxidized with high enantioselectivities using the fructose-derived chiral ketone 1 as catalyst and Oxone as oxidant. A detailed study of enantiomerically enriched enol ester epoxides has revealed that the acid-catalyzed rearrangement can proceed through two distinct pathways, one with retention of configuration and the other with inversion. The competition between the two pathways is highly dependent upon the nature of the acid catalyst. A strong acid favors retention of configuration and a weak acid favors inversion of configuration. Under thermal conditions, these epoxides rearrange highly stereoselectively with inversion of configuration. Either enantiomer of an α-acyloxy ketone can be formed from one enantiomer of an enol ester epoxide by judicious choice of reaction conditions.

Selective O-acylation of silyl enol ethers with acid halides mediated by a copper(I) salt

A new selective synthetic method of enol esters (O-acylated products) from silyl enol ether and acid chloride in the presence of CuCl is described. This reaction proceeds smoothly in DMI (1,3-dimethyl-2-imidazolidinone) but not in a less polar solvent. The silicon-copper exchange reaction pathway is proposed for this transformation as in the cases of D and alkynylsilane which were previously reported.

REACTION OF ENAMINOSILANE. SELECTIVE C-ACYLATION OF ENAMINOSILANES WITH ACID CHLORIDES.

In the presence of potassium fluoride and crown ether, acyl groups are introduced into the α-position of an imino group by acylation of enaminosilanes in good yields.