Engineering Center of Catalysis and Synthesis for Chiral Molecules, Department of Chemistry, Fudan University, Shanghai 200433, China.
Shanghai Engineering Center of Industrial Catalysis for Chiral Drugs, Shanghai 200433, China.
J Org Chem. 2020 Dec 4;85(23):14916-14925. doi: 10.1021/acs.joc.0c01583. Epub 2020 Oct 1.
Aryl benzofuranones are privileged structural units present in natural products and pharmaceutically relevant compounds with high bioactivity and therapeutic value; synthetic access to these scaffolds remains an area of intensive interest. A new and efficient TfOH-catalyzed cascade C-H activation/lactonization of phenols with α-aryl-α-diazoacetates is reported. This metal-free protocol provides an operationally simple and rapid method for the one-pot assembly of diverse α-aryl benzofuranones in high yields with broad substrate scope, a readily starting material, good chemo-regioselectivity, and excellent functional group compatibility.
芳基苯并呋喃酮是天然产物和具有高生物活性和治疗价值的药物相关化合物中存在的重要结构单元；因此，这些支架的合成方法仍然是一个备受关注的领域。本文报道了一种新的、有效的三氟甲磺酸（TfOH）催化的酚与α-芳基-α-重氮乙酸酯的级联 C-H 活化/内酯化反应。该无金属反应条件为各种α-芳基苯并呋喃酮的一锅法组装提供了一种操作简单、快速的方法，具有广泛的底物范围、易得的起始原料、良好的化学选择性和优异的官能团兼容性，以高产率得到目标产物。
