ETH Zürich, Vladimir-Prelog-Weg 3, HCI, 8093 Zürich, Switzerland.
J Am Chem Soc. 2020 Dec 16;142(50):20948-20955. doi: 10.1021/jacs.0c10832. Epub 2020 Dec 7.
We describe a general strategy for the intermolecular synthesis of polysubstituted cyclopentenones using palladium catalysis. Overall, this reaction is achieved via a molecular shuffling process involving an alkyne, an α,β-unsaturated acid chloride, which serves as both the alkene and carbon monoxide source, and a hydrosilane to create three new C-C bonds. This new carbon monoxide-free pathway delivers the products with excellent yields. Furthermore, the regioselectivity is complementary to conventional methods for cyclopentenone synthesis. In addition, a set of regio- and chemodivergent reactions are presented to emphasize the synthetic potential of this novel strategy.
我们描述了一种使用钯催化的分子间合成多取代环戊烯酮的通用策略。总的来说，该反应是通过一个分子混合过程实现的，涉及一个炔烃、一个α,β-不饱和酰氯，它既是烯烃又是一氧化碳的来源，还有一个硅烷，从而形成三个新的 C-C 键。这种新的无一氧化碳途径以优异的收率得到产物。此外，区域选择性与传统的环戊烯酮合成方法互补。此外，还提出了一组区域和化学发散反应，以强调这种新策略的合成潜力。
