Alkoxycarbonylation of 3,3,3‐Trifluoropropyne: an Intriguing Reaction to Prepare Trifluoromethyl‐Substituted Unsaturated Acid Derivatives

doi:10.1002/1615-4169(200207)344:5<543::AID-ADSC543>3.0.CO;2-U

Paper

Alkoxycarbonylation of 3,3,3‐Trifluoropropyne: an Intriguing Reaction to Prepare Trifluoromethyl‐Substituted Unsaturated Acid Derivatives

Published Jul 1, 2002 · A. Scrivanti, Valentina Beghetto, U. Matteoli

Advanced Synthesis & Catalysis

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Abstract

The addition of CO and methanol to 3,3,3-trifluoropropyne is catalysed by Pd(OAc)2 in the presence of (6-methylpyrid-2-yl)diphenylphosphine and CH3SO3H. The main products of the reaction are the methyl esters of 2-(trifluoromethyl)propenoic acid 1 and of 3-(trifluoromethyl)propenoic acid 2 (4,4,4-trifluorobut-2-enoic acid). The regioselectivity of the reaction can be controlled to a great extent by a suitable choice of the composition of the catalytic system and the reaction conditions. Thus, 1 can be obtained in 93% yield by using P(CO)=20 atm and high ligand/Pd and acid/Pd ratios. On the other hand, selectivity up to 85% in 2 can be achieved using P(CO)=80 atm and a low ligand/Pd ratio together with a high acid/Pd ratio. The reaction mechanism is also discussed.

Study Snapshot

The alkoxycarbonylation of 3,3,3-trifluoropropyne can produce trifluoromethyl-substituted unsaturated acid derivatives with high regioselectivity, depending on the composition of the catalytic system and reaction conditions.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Alkoxycarbonylation of 3,3,3‐Trifluoropropyne: an Intriguing Reaction to Prepare Trifluoromethyl‐Substituted Unsaturated Acid Derivatives

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