Photoinduced Tandem Cyanomethylation/Cyclization of Unsaturated Compounds: Access to Cyanomethylated 7- or 5-Membered <i>N</i>-Heterocycles
Changyou Guo, Li‐Jun Li, Qinqin Yan, Hongxun Zhou, Zhong‐Quan Liu, Zejiang Li
Abstract
A cyanomethylation/cyclization of aryl acetylenes/ethylenes with bromoacetonitrile was finished in a photopromoted condition, which offers an efficient and mild protocol for the preparation of cyanomethylated 7- or 5-membered N -heterocycles with good yields. Meanwhile, trichloroacetonitrile was also compatible with this radical pathway. In addition, a variety of single-crystal X-ray diffraction measurements, scaled-up operations to 1 mmol, functional group transformations of final products, light on/off experiments, and even radial inhibition studies were smoothly performed in this tandem system.
Topics & Concepts
TandemArylChemistryRadical cyclizationMedicinal chemistrySingle crystalStereochemistryOrganic chemistryCrystallographyMaterials scienceAlkylComposite materialRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques