High-Energy Ball Milling Enables an Ultra-fast Wittig Olefination Under Ambient and Solvent-free Conditions

DOI

Analytical Data and Compound Numbering (in paper numbering vs. ELN entries) for the Publication entitled:"High-Energy Ball Milling Enables an Ultra-fast Wittig Olefination Under Ambient and Solvent-free Conditions"

The paper was published on 2024-08-29 in Angewandte Chemie International Edition

Angew. Chem. Int. Ed. 2024, e202411536.

DOI: 10.1002/anie.202411536

Authors: Johanna Templ and Michael Schnürch

Funded by the Austrian Science Fund (FWF, project number P33064-N)

Context and methodology

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.

The publication and its Supporting Information can be found as open-access files on the publisher's website (see DOI above).

All detailed files containing the analytical raw data, for all compounds given in the Supporting Information of the manuscript are uploaded. An additional Word file named Angew. Chem. Int. Ed. 2024, e202411536_compound number list.pdf is uploaded, that should clearly link the compound number given in the paper to the respective entry in the ELN (jotempl) and the respective analytical data files. 

Technical details

The files uploded contain the FIDs of NMR spectra recorded by an in-house Bruker Spectrometer. A software to display NMR-spectra is needed, such as MestreNova or Topspin).

Identifier
DOI https://doi.org/10.48436/0cv9a-tfm43
Related Identifier IsOriginalFormOf https://doi.org/10.1002/anie.202411536
Related Identifier IsVersionOf https://doi.org/10.48436/ap13c-rkk65
Metadata Access https://researchdata.tuwien.ac.at/oai2d?verb=GetRecord&metadataPrefix=oai_datacite&identifier=oai:researchdata.tuwien.ac.at:0cv9a-tfm43
Provenance
Creator Templ, Johanna (ORCID: 0000-0002-4353-207X); Schnürch, Michael ORCID logo
Publisher TU Wien
Publication Year 2024
Funding Reference FWF Austrian Science Fund 013tf3c58 ROR P 33064 Substituting Gaseous Reagents for Solid Alternatives
Rights Creative Commons Attribution 4.0 International; https://creativecommons.org/licenses/by/4.0/legalcode
OpenAccess true
Contact tudata(at)tuwien.ac.at
Representation
Language English
Resource Type Dataset
Version 1.0.0
Discipline Other