Allylation of C-, N-, and O-Nucleophiles via a Mechanochemically-Driven Tsuji–Trost Reaction Suitable for Late-Stage Modification of Bioactive Molecules

2026-07-05T11:22:06Z https://researchdata.tuwien.ac.at/oai2d

oai:researchdata.tuwien.ac.at:pzh0v-8e846 2024-12-11T15:26:09Z openaire_data

4.3 TUW.TUDATA 10.48436/pzh0v-8e846 oai:researchdata.tuwien.ac.at:pzh0v-8e846 Templ, Johanna Johanna Templ 0000-0002-4353-207X TU Wien Schnürch, Michael Michael Schnürch 0000-0003-2946-9294 TU Wien Allylation of C-, N-, and O-Nucleophiles via a Mechanochemically-Driven Tsuji–Trost Reaction Suitable for Late-Stage Modification of Bioactive Molecules Angew. Chem. Int. Ed. 2024, 63, e202314637 TU Wien 2023 methodology solvent-free ball mill mechanochemistry Tsuji-Trost Allylation 2023-11-06 2023-09-29 2023-11-06 2024-12-11 eng 10.1002/anie.202314637 10.48436/qc7f9-zx172 1.0.0 Creative Commons Attribution 4.0 International Analytical Data and Compound Numbering (in paper numbering vs. ELN entries) for the Publication entitled:"Allylation of C-, N-, and O-Nucleophiles via a Mechanochemically-Driven Tsuji–Trost Reaction Suitable for Late-Stage Modification of Bioactive Molecules" The paper was published on 2023-22-06 in Angewandte Chemie International Edition Angew. Chem. Int. Ed. 2024, 63, e202314637 DOI: 10.1002/anie.202314637 Authors: Johanna Templ and Michael Schnürch Funded by the Austrian Science Fund (FWF, project number P33064-N) Context and methodology In this Publication, we describe a mechanochemical, solvent-free protocol for Tsuji–Trost allylation of O-, N-, and C-Nucleophiles using nontoxic, solid allyl trimethylammonium chloride as alternative allylating agent. This method features fast reaction kinetics, very low catalyst loadings, high yields, mild conditions, and high functional group tolerance. Its potential for late-stage modifications of bioactive compounds is demonstrated through multiple examples. 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, 63, e202314637_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). FWF Austrian Science Fund 013tf3c58 P 33064 Substituting Gaseous Reagents for Solid Alternatives