1,4-naphthoquinone derivative(Mahidol University)

This work demonstrates a simple, mild and efficient alkenyltrifluoromethylation of alkynes with readily available 2‐arylamino‐1,4‐naphthoquinones and Togni reagent as coupling partners. With 2‐arylamino‐1,4‐naphthoquinones as both photosensitizers and substrates, the title reaction proceeds smoothly in ethyl acetate under the irradiation of blue light, affording a series of CF3‐functionalized alkenes in excellent regio‐ and stereoselectivity. This protocol features good tolerance of functional groups, mild reaction conditions, green solvent and no involvement of external photocatalyst and additive. Furthermore, the further modification of bioactive molecules such as Menthol, Levocetirizine and Indometacin, and the late‐stage transformations of the resulting CF3‐functionalized alkenes are accomplished.

An electrooxidative C-C coupling between arylhydrazines and aminoquinones has been developed for the construction of aryl-substituted aminoquinones, which features excellent chemo- and regioselectivity. Mechanistic studies support the idea that the denitrogenative formation of aryl radicals might be involved in the metal-free C-H arylation.