55285-80-8

Upstream product

• 611-10-9 2-ethoxycarbonyl-1-cyclopentanone 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 98-80-6 phenylboronic acid 
• 587-85-9 diphenylmercury(II) 
• 47252-14-2 triphenylbismuth carbonate 
• 507233-69-4 triphenyl bismuth ⁽²⁺⁾; dichloride 
• 60221-80-9 benzylphenylmercury 
• 3076-54-8 phenyllead(IV) triacetate 
• 628-20-6 4-Chlorobutyronitrile 
• 1403893-43-5 C₁₀H₁₁BrO₂Zn 
• 66003-76-7 Diphenyliodonium triflate 
• 214534-44-8 diphenyliodonium (1S)-camphor-10-sulfonate 

Downstream Products

• 156006-03-0 2-Phenyl-bicyclo[3.1.0]hexane-2-carboxylic acid 2-thioxo-2H-pyridin-1-yl ester 
• 156006-05-2 2-Phenyl-bicyclo[3.1.0]hexane-2-carboxylic acid ethyl ester 
• 156006-04-1 1-Phenyl-cyclopent-2-enecarboxylic acid ethyl ester 
• 156006-06-3 2-Phenyl-bicyclo[3.1.0]hexane-2-carboxylic acid 
• 55285-93-3 1-Phenyl-2-thioxo-cyclopentanecarboxylic acid ethyl ester 
• 55285-87-5 2-Mercapto-1-phenyl-cyclopent-2-enecarboxylic acid ethyl ester 

Relevant academic research and scientific papers

Catalytic asymmetric intramolecular homologation of ketones with α-diazoesters: Synthesis of cyclic α-Aryl/Alkyl β-ketoesters

A catalytic asymmetric intramolecular homologation of simple ketones with α-diazoesters was firstly accomplished with a chiral N,N′-dioxide-Sc(OTf)3 complex. This method provides an efficient access to chiral cyclic α-aryl/alkyl β-ketoesters containing an all-carbon quaternary stereocenter. Under mild conditions, a variety of aryl- and alkyl-substituted ketone groups reacted with α-diazoester groups smoothly through an intramolecular addition/rearrangement process, producing the β-ketoesters in high yield and enantiomeric excess.

Tandem one-pot construction of indoles via palladium and copper-catalyzed coupling reactions of the blaise reaction intermediate

The palladium-catalyzed intramolecular N-arylation of the Blaise reaction intermediate, formed by reaction of nitriles with an in situ generated Reformatsky reagent from ethyl -bromo - (2-bromophenyl)acetate and zinc, afforded indoles in good yields. Exte

α-Arylation by rearrangement: On the reaction of enolates with diaryliodonium salts

Surprising equilibration: A new mechanism for the title reaction is supported by DFT calculations and experimental observations. The C-I and OI intermediates are isoenergetic and equilibrate quickly. Thus, any chiral information induced in the initial complex will be destroyed. In the final CC bond-forming step, a [2,3]-rearrangement from the O-I bonded intermediate is slightly preferred over the [1,2]elimination from the C-I bonded isomer (see scheme). (Figure Presented)

Arylations mediated by lead(IV) in the presence of formazan and imine ligands

The use of formazan and imine ligands in arylations of β-dicarbonyl systems by phenyl boronic acid/lead(IV) carboxylates is examined.

The direct acyl-alkylation of arynes

An efficient and mild acyl-alkylation of arynes is described. The method is used to synthesize medium-sized carbocycles by the ring-expansion of cyclic β-ketoesters. Copyright

Reaction of Arylboronic Acids and their Derivatives with Lead Tetra-acetate. The Generation of Aryl-lead Triacetates, and meta- and para-Phenylenebis(lead triacetate), in situ for Electrophilic Arylation

Arylboronic acids and some of their derivatives have been found to undergo a rapid boron-lead exchange with lead tetra-acetate.In the presence of a catalytic amount of mercury(II) acetate, the reaction produces mainly the aryl-lead triacetate, and it has been developed as a convenient method for in situ generation of these useful electrophilic C-arylating reagents.The reaction allows the generation for the first time of meta- and para-phenylenebis(lead triacetate), compounds which behave as meta- and para-phenylene dication equivalents.

Arylation with Aryllead Triacetates Produced in situ by Mercury-Lead Exchange

The addition of lead tetraacetate to diphenylmercury in chloroform leads to the rapid formation of a solution of phenyllead triacetate, which has been used directly for the C-phenylation of ethyl 2-oxocyclopentanecarboxylate (1) and 2-nitropropane in good

Pentavalent Organobismuth Reagents. Part 3. Phenylation of Enols and of Enolate and other Anions

The phenylation of enols and of enolate anions of ketones, β-diketones and keto esters has been studied using a range of Bi reagents.Under basic conditions C-phenylation is observed and, even hindered, perphenylated compounds are easily synthesized.Under neutral and acidic conditions ordinary ketones do not react and enolic systems give O-phenylation.A number of other anions have been phenylated under basic conditions, including the key compound indole wich mainly gave 3-C-phenylation.All these reactions can be supposed to have one of two alternative mechanisms, which parallel the two mechanisms proposed for the phenylation of phenols.

ARYLATION WITH ARYLLEAD TRIACETATES PRODUCED IN SITU BY MERCURY-LEAD EXCHANGE

Reaction of a diarylmercury with lead tetraacetate to give an aryllead triacetate has been found to be a rapid reaction.The in situ generation of aryllead triacetates is thus an attractive alternative to the use of the purified reagents in the various electrophilic arylation reactions of these compounds.