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Alkynyl Phenyl Selenides as Intermediates in the Metal‐Free Cyclisation of N‐Tosyl Homopropargyl Amides to γ‐Lactams
European Journal of Organic Chemistry ( IF 2.5 ) Pub Date : 2024-12-23 , DOI: 10.1002/ejoc.202401248 Andrea Temperini, Giulia Brufani, Stefano Santoro, Luigi Vaccaro
European Journal of Organic Chemistry ( IF 2.5 ) Pub Date : 2024-12-23 , DOI: 10.1002/ejoc.202401248 Andrea Temperini, Giulia Brufani, Stefano Santoro, Luigi Vaccaro
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.
中文翻译:
炔基苯基硒化物作为 N-甲苯基高炔酰胺无金属环化为 γ-内酰胺的中间体
在这项工作中,我们提出了一种高效的 Brønsted 酸催化的分子内氢胺化反应,即高炔丙基 N-甲苯基酰胺,通过相应的炔基苯基硒化物中间体生产合成有用的取代 γ-内酰胺。我们专注于在流动条件下优化环化方案,从而显著提高了效率,从而减少了该过程所需的时间和资源。还对模型炔基苯基硒化物催化转化的反应机理进行了 DFT 计算。
更新日期:2024-12-23
中文翻译:
炔基苯基硒化物作为 N-甲苯基高炔酰胺无金属环化为 γ-内酰胺的中间体
在这项工作中,我们提出了一种高效的 Brønsted 酸催化的分子内氢胺化反应,即高炔丙基 N-甲苯基酰胺,通过相应的炔基苯基硒化物中间体生产合成有用的取代 γ-内酰胺。我们专注于在流动条件下优化环化方案,从而显著提高了效率,从而减少了该过程所需的时间和资源。还对模型炔基苯基硒化物催化转化的反应机理进行了 DFT 计算。