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Platinum- and gold-catalyzed hydroalkoxylation and tetramerization of propiolate esters

Paper ID Volume ID Publish Year Pages File Format Full-Text
49437 46745 2014 5 PDF Available
Title
Platinum- and gold-catalyzed hydroalkoxylation and tetramerization of propiolate esters
Abstract

•PtCl2-catalyzed hydroalkoxylation of propiolate esters affords (E)-vinyl ethers.•PtCl2-catalyzed bis(hydroalkoxylation) of propiolate esters affords acetals.•AuCl3-catalyzed tetramerization of propiolate esters affords cyclooctatetraenes.

PtCl2 was found to efficiently catalyze intermolecular additions of propiolate esters with alcohols. The reaction of propiolate esters and alcohols in the presence of PtCl2 gave (E)-vinyl ethers as the major products at 60 °C, whereas alkyl 3,3-dialkoxypropanoates were predominantly obtained when the reaction temperature was set to 80 °C. On the other hand, a novel regioselective tetramerization of propiolate esters catalyzed by AuCl3 under mild conditions afforded 1,2,5,6-tetrasubstituted-cyclooctatetraene (1,2,5,6-COT) in moderate yields.

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Keywords
Hydroalkoxylation; Tetramerization; Propiolate ester; Platinum catalyst; Gold catalystFMVJYQGSRWVMQV-UHFFFAOYSA-N; UNONUCVWBGLFIO-SNAWJCMRSA-N; VHJGYBJBTJCULO-UHFFFAOYSA-N; NAFJQHIPQGWUSC-GABLAEFESA-N
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Platinum- and gold-catalyzed hydroalkoxylation and tetramerization of propiolate esters
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Publisher
Database: Elsevier - ScienceDirect
Journal: Catalysis Communications - Volume 56, 5 November 2014, Pages 101–105
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
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