Regiocontrolled Ru-catalyzed addition of carboxylic acids to alkynes: practical protocols for the synthesis of vinyl esters

Lukas J. Goossen; Jens Paetzold; Debasis Koley

doi:10.1039/B211277A

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Chemical Communications

Issue 6, 2003

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Regiocontrolled Ru-catalyzed addition of carboxylic acids to alkynes: practical protocols for the synthesis of vinyl esters

Lukas J. Goossen , Jens Paetzold and Debasis Koley

Chem. Commun., 2003, 706-707

DOI: 10.1039/B211277A
Received 14 Nov 2002, Accepted 28 Jan 2003
First published on the web 17 Feb 2003

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The catalytic activity of commercially available, air and water stable ruthenium complexes in the addition of carboxylic acids to terminal alkynes was found to be drastically enhanced by the addition of small quantities of base. Moreover, the regioselectivity of the reaction can be controlled by the choice of the base so that both the Markovnikov (Na₂CO₃) and the anti-Markovnikov products (DMAP) are now easily accessible in excellent selectivities.

Abstract from Methods in Organic Synthesis 2003

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Abstract from Catalysts & Catalysed Reactions 2003

Catalytic activity was drastically enhanced by addition of small quantities of base, the choice of which controls the regioselectivity so that both the Markovnikov (Na2CO3) and the anti-Markovnikov (DMAP) products could be synthesised.

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Chemical Communications

Regiocontrolled Ru-catalyzed addition of carboxylic acids to alkynes: practical protocols for the synthesis of vinyl esters

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