Water as a Reactant:\nDABCO-Catalyzed Hydration of\nActivated Alkynes for the Synthesis of Divinyl Ethers

A practical and efficient addition of water to readily\navailable\nactivated alkynes delivering divinyl ethers is reported. The reaction\nproceeds with full atom economy in a very straightforward experimental\nprocedure. Additionally, of all the tertiary amines studied to catalyze\nthe reaction, the best and most efficient is clearly DABCO (1,4-diazabicyclo[2.2.2]octane).\nFinally, the solvent choice is crucial for the efficiency of this\nprocess and we have found that the reaction is best performed in wet\ndichloromethane for propiolic esters and alkynones, and in wet acetonitrile\nfor propiolamides.

Publication Details

Journal
Figshare
Published
2024-09-30
DOI
https://doi.org/10.1021/acs.joc.4c01815.s001
Primary Topic
Cyclopropane Reaction Mechanisms
Type
article
Field-Weighted Citation Impact
0.00
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article

Water as a Reactant:\nDABCO-Catalyzed Hydration of\nActivated Alkynes for the Synthesis of Divinyl Ethers

Figshare
Cyclopropane Reaction Mechanisms
article

Water as a Reactant:\nDABCO-Catalyzed Hydration of\nActivated Alkynes for the Synthesis of Divinyl Ethers

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Abstract

A practical and efficient addition of water to readily\navailable\nactivated alkynes delivering divinyl ethers is reported. The reaction\nproceeds with full atom economy in a very straightforward experimental\nprocedure. Additionally, of all the tertiary amines studied to catalyze\nthe reaction, the best and most efficient is clearly DABCO (1,4-diazabicyclo[2.2.2]octane).\nFinally, the solvent choice is crucial for the efficiency of this\nprocess and we have found that the reaction is best performed in wet\ndichloromethane for propiolic esters and alkynones, and in wet acetonitrile\nfor propiolamides.

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Clean water and sanitation
Openalex Percentile: Top 72%
Cyclopropane Reaction Mechanisms
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Water as a Reactant:\nDABCO-Catalyzed Hydration of\nActivated Alkynes for the Synthesis of Divinyl Ethers · Figshare (2024) | TGRS Research Map | TGRS