24647-07-2

Upstream product

• 451-40-1 phenyl benzyl ketone 
• 108-24-7 acetic anhydride 
• 82352-02-1 (Z)-α-acetoxy-β-(acetoxymercuri)stilbene 
• 64-19-7 acetic acid 
• 501-65-5 diphenyl acetylene 
• 1600-27-7 mercury(II) diacetate 
• 16188-33-3 cis-stilben-α-ylmercury (1+); chloride 

Downstream Products

• 1678-43-9 1-benzoyl-1-phenylmethyl p-toluenesulfonate 
• 58-72-0 Triphenylethylene 
• 451-40-1 phenyl benzyl ketone 

Relevant academic research and scientific papers

Visible light induced C-H monofluoroalkylation to synthesize 1,4-unsaturated compound

We developed a method to synthesize fluorinated 1,4-unsaturated dicarbonyl compounds via photoredox catalyzed radical addition process. Commercially available ethyl bromodifluoroacetate (BrCF2CO2Et) as fluoroalkyl source, the corresponding fluoro-containing dicarbonyl compounds could be obtained in moderate to good yields.

Enol Ester Synthesis via Cobalt-Catalyzed Regio- and Stereoselective Addition of Carboxylic Acids to Alkynes

A cobalt-catalyzed highly regio- and stereoselective hydro-oxycarbonylation of alkynes is reported. Both terminal and internal alkynes can react with carboxylic acids to afford enol esters in high yields. The catalyst generated from Co(BF4)2, tridentate phosphine ligand L5, and zinc in situ exhibits much higher reactivity than the corresponding cobalt/diphosphine complex.

Gold(I)-catalyzed addition of carboxylic acids to alkynes

Au(I)-catalyzed hydroacyloxylation of alkynes with carboxylic acids is described. PPh3AuCl/AgPF6 catalyst affords the Markonikov addition products, whereas PPh3AuCl/AgOTf catalyst gives the more stable isomerized products

Addition of carboxylic acids to alkynes catalysed by ruthenium complexes

The addition of carboxylic acids to alkynes has been found to be catalyzed by Ru3(CO)12 as well as by dimeric ruthenium carboxylate complexes of general structure 2.The reaction yields vinyl esters.It was found to be general with respect

SYNTHESIS OF ENOL ESTERS FROM TERMINAL ALKYNES CATALYZED BY RUTHENIUM COMPLEXES

Regioselective enol ester formation results from the addition of saturated and unsaturated carboxylic acids to phenylacetylene in the presence of RuCl3, RuCl3/2PR3 or RuCl2(PMe3)(arene) catalysts.

Stereochemistry of the Acetoxymercuration of Alkynes. A Synthesis of Vinyl Acetates

The stereochemistry of acetoxymercuration of 3-hexyne has been established as antarafacial on the basis of an X-ray crystallographic study.Acetoxymercuration of diphenylacetylene afforded (Z)-α-acetoxy-β-(acetoxymercuri)stilbene by a suprafacial addition of Hg(OAc)2.A simple method for the in situ acetoxymercuration-demercuration of dialkyl-substituted alkynes to afford vinyl acetates is described.The sodium borohydride reduction of vinyl mercurials was shown to produce divinyl mercurials while demercuration with zinc dust in acetic acid provided a useful method for the preparation of vinyl acetates.

Regio- and Stereo-selectivity of Acetoxymercuration of Acetylenes

Acetoxymercuration of alkylphenylacetylenes (PhCCR; R = Me, Et, Prn, or Bun) (1) in acetic acid at 20 - 60 deg C proceeds completely in a trans-fashion to afford a regioisomeric mixture of two vinylmercury(II) compounds, Ph(OAc)C=C(HgCl)R (2) and Ph(HgCl)C=C(OAc)R (3), the extent of attack of Hg at the carbon α to alkyl group to form (2) being increased upon increasing the carbonyl chain length of the alkyl group .A bridged mercurinium ion intermediate in which phenyl and alkyl groups are bent toward the attacking side of acetate anion is proposed for explaining a marked dependence of the isomer ratio (2):(3) on the kind of alkyl groups.Similar treatment of diphenylacetylene at 20 - 95 deg C gives only the cis-adduct as reported previously, while that of diethyl-acetylene affords the trans-adduct and a mixture of trans- and cis-adduct at 20 deg C and at 65 deg C, respectively.The NaBH4 reduction of (2, R = Me) in neutral condition produces a mixture of (Z)- and (E)-1-acetoxy-1-phenylpropene (ca. 3-5:1) in contrast to the reduction of thallium analogue of (2) which gives only the Z-isomer.