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.

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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

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article

Alkynyl Phenyl Selenides as Intermediates in the Metal‐Free Cyclisation of N‐Tosyl Homopropargyl Amides to γ‐Lactams

Andrea Temperini, Luigi Vaccaro, Stefano Santoro, Giulia Brufani
2 citations
European Journal of Organic Chemistry
Catalytic Alkyne Reactions
0.50
article

Alkynyl Phenyl Selenides as Intermediates in the Metal‐Free Cyclisation of N‐Tosyl Homopropargyl Amides to γ‐Lactams

Andrea Temperini, Luigi Vaccaro, Stefano Santoro, Giulia Brufani
article en
2 citations

Abstract

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.

European Journal of Organic ChemistryVol. 28(8)
University of Perugia (IT)
European Commission
Openalex Percentile: Top 37%
Catalytic Alkyne Reactions
0.50
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