Department of Chemistry, Roy and Diana Vagelos Laboratories, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, United States.
Org Lett. 2021 Jan 15;23(2):433-437. doi: 10.1021/acs.orglett.0c03941. Epub 2021 Jan 4.
A copper-catalyzed carbochlorination of alkenes with aryl malononitriles and chloride is disclosed. This net oxidative transformation proceeds with activated and unactivated alkenes with moderate to excellent yields. Mechanism experiments suggest addition of the malononitrile radical to form a secondary carbon radical which is intercepted by a chloride source. The resultant products can be transformed into biologically important γ-lactones in one further step.
公开了一种铜催化的烯烃与芳基丙二腈和氯化物的碳氯化反应。这种净氧化转化可在活化和未活化的烯烃中进行,产率中等至优秀。机理实验表明,丙二腈自由基加成形成仲碳自由基,该自由基被氯化物源捕获。所得产物可以进一步转化为具有生物重要性的γ-内酯。