Graduate School of Pharmaceutical Science, Tohoku University, Aoba, Sendai, 980-8578, Japan.
Chemistry. 2020 Apr 6;26(20):4496-4499. doi: 10.1002/chem.201905777. Epub 2020 Mar 18.
β-Lactams are important structural motifs because of their ubiquity in natural products and pharmaceuticals. We report herein a Cu-catalyzed intramolecular oxidative C(sp )-H amidation for the synthesis of β-lactams using tBuOOtBu. This method is based on Kharasch-Sosnovsky amidation and does not require prefunctionalization of C(sp )-H bonds or the installation of a directing group, thereby allowing for the straightforward synthesis of β-lactams. Our intramolecular functionalization protocol can be extended to diverse benzylic C(sp )-H bonds and shows excellent functional-group tolerance.
β-内酰胺因其在天然产物和药物中的普遍存在而成为重要的结构基序。我们在此报告了一种使用 tBuOOtBu 的 Cu 催化的分子内氧化 C(sp )-H 酰胺化反应，用于合成β-内酰胺。该方法基于 Kharasch-Sosnovsky 酰胺化，不需要对 C(sp )-H 键进行预官能化或安装导向基团，从而可以直接合成β-内酰胺。我们的分子内官能团化方案可以扩展到各种苄基 C(sp )-H 键，并表现出优异的官能团耐受性。
