Golagani Durga, Prakash Kota Krishna, Thapa Satyam, Sai Naik Mudavath Bhargav, Akondi Srirama Murthy
Department of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500007, India.
Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India.
Org Lett. 2024 Oct 11;26(40):8583-8588. doi: 10.1021/acs.orglett.4c03216. Epub 2024 Oct 1.
A novel photoinduced Fe(OTf)/2,4,6-collidine-catalyzed alkylation of Morita-Baylis-Hillman (MBH) acetates using carboxylic acids in a regio- and stereoselective manner is reported. This method demonstrates a broad scope, encompassing various carboxylic acids and MBH acetates, including drugs and bioactive molecules, to synthesize densely functionalized cinnamates and acrylates. The reactions are performed in the green solvent dimethyl carbonate under oxidant-free conditions. Based on control experiments, a plausible mechanism involving an Fe(II)-Fe(III)-Fe(II) cycle is proposed.
报道了一种新型的光诱导Fe(OTf)/2,4,6-可力丁催化的Morita-Baylis-Hillman（MBH）乙酸酯与羧酸的区域和立体选择性烷基化反应。该方法适用范围广泛，涵盖各种羧酸和MBH乙酸酯，包括药物和生物活性分子，可用于合成功能密集的肉桂酸酯和丙烯酸酯。反应在绿色溶剂碳酸二甲酯中于无氧化剂条件下进行。基于对照实验，提出了一种涉及Fe(II)-Fe(III)-Fe(II)循环的合理机制。
