132709-18-3

Upstream product

• 201230-82-2 carbon monoxide 
• 536-74-3 phenylacetylene 
• 108-95-2 phenol 
• 492-38-6 2-phenylacrylic acid 
• 26190-67-0 toluene-4-sulfonic acid 1-phenylvinyl ester 
• 1864-94-4 phenyl formate 
• 98-86-2 acetophenone 
• 98-81-7 1-bromovinylbenzene 

Downstream Products

• 842163-64-8 (+/-)-phenyl 3-methyl-5-phenyl-2-isoxazoline-5-carboxylate 
• 1264519-53-0 C₂₃H₂₄O₄ 
• 842163-66-0 (+/-)-5-hydroxymethyl-3-methyl-5-phenyl-2-isoxazoline 

Relevant academic research and scientific papers

Markovnikov-Selective Palladium Catalyst for Carbonylation of Alkynes with Heteroarenes

A new class of palladium catalysts, based on heterocyclic diphosphines, was rationally designed and synthesized. Application of one of these catalysts allows novel Markovnikov-selective carbonylation of non-activated alkynes with heteroarenes to give the

Palladium-catalyzed carbonylation of aryl, alkenyl, and allyl halides with phenyl formate

Highly efficient palladium-catalyzed carbonylation of aryl, alkenyl, and allyl halides with phenyl formate is reported. This procedure does not use carbon monoxide and affords one-carbon-elongated carboxylic acid phenyl esters in excellent yields. The reaction proceeds smoothly under mild conditions and tolerates a wide range of functional groups including aldehyde, ether, ketone, ester, and cyano groups. Furthermore, a variety of heteroaromatic bromides can be converted to the corresponding phenyl esters in high yields.

Preparation of α,β-unsaturated esters and amides via external-CO-free palladium-catalyzed carbonylation of alkenyl tosylates

Palladium-catalyzed carbonylation of tosylates with phenyl formate is described. This procedure needs neither external carbon monoxide nor any pressure-resistant apparatus. A variety of cyclic and acyclic alkenyl tosylates can be converted into the corresponding phenyl esters in good yields. Furthermore, this method is effective for the one-pot synthesis of α,β-unsaturated amides.

Palladium-catalyzed hydroesterification of alkynes employing aryl formates without the use of external carbon monoxide

A highly efficient hydroesterification of alkynes employing aryl formates has been developed without the use of external carbon monoxide and at ambient pressure. The reaction in the presence of a palladium-xantphos catalyst system selectively affords α,β-unsaturated esters in good to high yields. Use of an aryl formate is crucial and alkyl formates did not react at all. The hydroesterification of norbornene and terminal alkenes also readily proceeded under similar reaction conditions. A mechanistic study showed that conversion of aryl formates to carbon monoxide and phenol derivatives occurred in the hydroesterification. Xantphos is highly effective as a ligand both in the conversion of aryl formates and the hydroesterification reactions.

Chemoenzymatic synthesis of primary alcohols with a 2-isoxazoline moiety

Racemic 2-isoxazoline-5-carboxylate esters were reduced under mild conditions to form the corresponding primary alcohols. These alcohols were enzymically resolved by acylation with succinic anhydride in the presence of Amano AK lipase.

PALLADIUM-CATALYZED ARYLOXYCARBONYLATION OF TERMINAL ALKYNES

Carbonylation of terminal alkynes using palladium-phosphine complexes proceeds efficiently in the presence of 3- or 4-substituted phenols to give the corresponding 2-substituted 2-propenoic acid aryl esters in good selectivity and yield.