Work

Water as a Reactant: DABCO-Catalyzed Hydration of Activated Alkynes for the Synthesis of Divinyl Ethers

Year: 2024

Type: article

Abstract: A practical and efficient addition of water to readily available activated alkynes delivering divinyl ethers is reported. The reaction proceeds with full atom economy in a very straightforward experimental procedure. Additionally, of all the tertiary amines studied to catalyze the reaction, the best and most efficient is clearly DABCO (1,4-diazabicyclo[2.2.2]octane). Finally, the solvent choice is crucial for the efficiency of this process and we have found that the reaction is best performed in wet dichloromethane for propiolic esters and alkynones, and in wet acetonitrile for propiolamides.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.4c01815

Authors: Raquel Diana-Rivero, David S. Rivero, Alba García-Martín, Romen Carrillo, David Tejedor

Institutions: Consejo Superior de Investigaciones Científicas, Instituto de Productos Naturales y Agrobiología

Language: English

Topic: Catalytic Alkyne Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: Ministerio de Ciencia, Innovación y Universidades, European Commission, Cabildo de Tenerife, Agencia Estatal de Investigación