Alkynyl Phenyl Selenides as Intermediates in the Metal‐Free Cyclisation of <i>N</i>‐Tosyl Homopropargyl Amides to γ‐Lactams
Abstract In this work, we present an efficient Brønsted acid‐catalysed intramolecular hydroamination reaction of homopropargyl N‐tosyl amides to produce synthetically useful substituted γ‐lactams through the corresponding alkynyl phenyl selenide intermediates. Our focus on optimising the cyclisation protocol under flow conditions has led to a significant enhancement in efficiency, thereby reducing the time and resources required for the process. DFT calculations of the reaction mechanism for the catalytic transformation of a model alkynyl phenyl selenide were also conducted.
Authors
- Andrea Temperini (ORCID: https://orcid.org/0000-0001-8702-2082)
- Luigi Vaccaro (ORCID: https://orcid.org/0000-0003-4168-2303)
- Stefano Santoro (ORCID: https://orcid.org/0000-0003-0223-1489)
- Giulia Brufani
Institutions
- University of Perugia (IT)
Publication Details
- Journal
- European Journal of Organic Chemistry
- Published
- 2024-12-23
- DOI
- https://doi.org/10.1002/ejoc.202401248
- Citations
- 2
- Primary Topic
- Catalytic Alkyne Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.50
Funders
- European Commission