High‐Energy Ball Milling Enables an Ultra‐Fast Wittig Olefination Under Ambient and Solvent‐free Conditions

30 Seconds to success!-The Wittig reaction, a fundamental and extensively utilized reaction in organic chemistry, enables the efficient conversion of carbonyl compounds to olefins using phosphonium salts. Traditionally, meticulous reaction setup, including the pre-formation of a reactive ylide species via deprotonation of a phosphonium salt, is crucial for achieving high-yielding reactions under classical solution-based conditions. In this report, we present an unprecedented protocol for an ultra-fast mechanically induced Wittig reaction under solvent-free and ambient conditions, often eliminating the need for tedious ylide pre-formation under strict air and moisture exclusion. A range of aldehydes and ketones were reacted with diverse phosphonium salts under high-energy ball milling conditions, frequently giving access to the respective olefins in only 30 seconds.

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Publication Details

Journal
Angewandte Chemie International Edition
Published
2024-08-29
DOI
https://doi.org/10.1002/anie.202411536
Citations
22
Primary Topic
Phosphorus compounds and reactions
Type
article
Field-Weighted Citation Impact
5.50

Funders

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article

High‐Energy Ball Milling Enables an Ultra‐Fast Wittig Olefination Under Ambient and Solvent‐free Conditions

Johanna Templ, Michael Schnürch
22 citations
Angewandte Chemie International Edition
Phosphorus compounds and reactions
5.50
article

High‐Energy Ball Milling Enables an Ultra‐Fast Wittig Olefination Under Ambient and Solvent‐free Conditions

Johanna Templ, Michael Schnürch
article en
22 citations

Abstract

30 Seconds to success!-The Wittig reaction, a fundamental and extensively utilized reaction in organic chemistry, enables the efficient conversion of carbonyl compounds to olefins using phosphonium salts. Traditionally, meticulous reaction setup, including the pre-formation of a reactive ylide species via deprotonation of a phosphonium salt, is crucial for achieving high-yielding reactions under classical solution-based conditions. In this report, we present an unprecedented protocol for an ultra-fast mechanically induced Wittig reaction under solvent-free and ambient conditions, often eliminating the need for tedious ylide pre-formation under strict air and moisture exclusion. A range of aldehydes and ketones were reacted with diverse phosphonium salts under high-energy ball milling conditions, frequently giving access to the respective olefins in only 30 seconds.

Angewandte Chemie International EditionVol. 63(49)
TU Wien (AT)
Austrian Science Fund
Affordable and clean energy
Openalex Percentile: Top 3%
Phosphorus compounds and reactions
5.50
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