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.

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

Temperini, Andrea
;
Brufani, Giulia;Santoro, Stefano;Vaccaro, Luigi
2025

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.
2025
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11391/1613474
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