用于从叔酰胺和卤代烃形成C(sp)-C(sp)键的全自动流动协议。
Fully Automated Flow Protocol for C(sp)-C(sp) Bond Formation from Tertiary Amides and Alkyl Halides.
作者信息
Pijper Brenda, Martín Raúl, Huertas-Alonso Alberto J, Linares Maria Lourdes, López Enol, Llaveria Josep, Díaz-Ortiz Ángel, Dixon Darren J, de la Hoz Antonio, Alcázar Jesús
机构信息
Global Discovery Chemistry, Janssen Research and Development, Janssen-Cilag, S. A., Jarama 75 A, 45007 Toledo, Spain.
Facultad de Ciencias Químicas, Universidad de Castilla-La Mancha, Av. Camilo José Cela 10, 13071 Ciudad Real, Spain.
出版信息
Org Lett. 2024 Apr 12;26(14):2724-2728. doi: 10.1021/acs.orglett.3c01390. Epub 2023 May 23.
Herein, we present a novel C(sp)-C(sp) bond-forming protocol via the reductive coupling of abundant tertiary amides with organozinc reagents prepared from their corresponding alkyl halides. Using a multistep fully automated flow protocol, this reaction could be used for both library synthesis and target molecule synthesis on the gram-scale starting from bench-stable reagents. Additionally, excellent chemoselectivity and functional group tolerance make it ideal for late-stage diversification of druglike molecules.
在此，我们展示了一种通过大量叔酰胺与由相应卤代烃制备的有机锌试剂进行还原偶联来形成新型C(sp)-C(sp)键的方法。使用多步全自动流动方法，该反应可用于从稳定试剂开始的克级文库合成和目标分子合成。此外，出色的化学选择性和官能团耐受性使其成为类药物分子后期多样化的理想选择。
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