261759-73-3

Upstream product

• 4187-87-5 1-Phenyl-2-propyn-1-ol 
• 536-74-3 phenylacetylene 
• 100-52-7 benzaldehyde 
• 6738-06-3 phenylethynylmagnesium bromide 
• 1817-49-8 1,3-diphenyl-1-propyn-3-ol 
• 79-22-1 methyl chloroformate 

Downstream Products

• 1314111-26-6 1,3,4-triphenylpenta-1,2,4-triene 
• 53395-25-8 1,1'-(3-methoxyprop-1-yne-1,3-diyl)dibenzene 
• 614-47-1 1,3-diphenyl-propen-3-one 
• 1191257-51-8 (3R,4S,Z)-benzyl 2-benzylidene-3-phenylchroman-4-carboxylate 
• 1351953-58-6 2-(1,3-dithiolan-2-ylidene)-1,3,5-triphenylpent-4-yn-1-one 
• 1045346-80-2 1-cyclopropyl-1,3-diphenylpropadiene 
• 53544-89-1 1,1'-(1-methyl-1,2-propadiene-1,3-diyl)bisbenzene 

Relevant academic research and scientific papers

Gold(I)-catalyzed decarboxylation of propargyl carbonates: Reactivity reversal of the gold catalyst from π-Lewis acidity to σ-Lewis acidity

A cationic gold(I)-catalyzed decarboxylative etherification of propargyl carbonates to selectively produce propargyl ethers is reported. In the reaction the gold(I) catalyst shows a distinct σ-Lewis acidity rather than the commonly observed π-Lewis acidity, and thus catalyzes the decarboxylation of a variety of propargyl carbonates to give the corresponding propargyl ethers with high selectivity. This reaction represents a rare example of the tunable reactivity of cationic gold(I) complexes between σ-Lewis acidity and π-Lewis acidity.

Palladium-catalyzed coupling of propargylic carbonates with N-tosylhydrazones: Highly selective synthesis of substituted propargylic N-sulfonylhydrazones and vinylallenes

An efficient palladium-catalyzed coupling of propargylic carbonates (1) with N-tosylhydrazones (2, 2′) has been carried out. A wide range of propargylic N-sulfonylhydrazones (3) and multisubstituted vinylallenes (4) can be obtained selectively by using either [PdCl2(CH3CN) 2] or [Pd2(dba)3] as catalysts. (dba=trans,trans-dibenzylideneacetone, dppp=propane-l,3- diylbis(diphenylphosphane), Ts=4-toluenesulfonyl.) Copyright

Stereoselective construction of substituted chromans by palladium-catalyzed cyclization of propargylic carbonates with 2-(2-Hydroxyphenyl)acetates

Highly substituted chromans have been constructed In a highly stereoselective manner by a palladium-catalyzed reaction of propargylic carbonates with 2-(2-hydroxyphenyl)acetates. Enantioselective reactions also successfully proceeded to give the optically active chromans with high enantioselectivity.

Palladium-catalyzed synthesis of 2,3-dihydro-2-ylidene-1,4-benzodioxins

Palladium-catalyzed condensation of benzene-1,2-diol with various propargylic carbonates, afforded regio- and stereoselectively 2,3-dihydro-2-ylidene-1,4-benzodioxins. The reaction is suggested to proceed by the formation of a (σ-allenyl)palladium complex, followed by the intermolecular attack of the phenoxide ion on this complex to generate a new (σ-allyl)palladium complex in equilibrium with the corresponding (η3-allyl)palladium complex. Intramolecular attack of the phenoxide ion afforded the corresponding benzodioxan compound. This last attack occurs predominantly at the more electrophilic end of the (η3-allyl)palladium intermediate. The Z- or E-stereochemistry of the products was established by 1H NMR and proton NOE measurements and also by X-ray analysis on an example. The Z-stereochemistry generally observed is in agreement with the formation of this (η3-allyl)palladium intermediate. However, in the case of tertiary propargylic carbonates, the E-stereochemistry generally observed could be explained by an intramolecular attack of the phenoxide ion on the intermediate (σ-allyl)palladium complex, in slow equilibrium with the (η3allyl)palladium complex.