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Lewis Acid-Mediated Regioselective Hydrofunctionalization of Styrenes with Isatins and Heterocycles
Shengxiang Qin1, Yunshi Liao1, Qiang Ni1
1School of Chemistry, IGCME, The Key Laboratory of Low-Carbon Chemistry & Energy Conservation of Guangdong Province, Guangdong Provincial Key Laboratory of Chiral Molecules and Drug Discovery, Sun Yat-sen University, Guangzhou 510006, People's Republic of China.
Abstract:
The ligand-free Lewis acid-mediated regioselective hydroamination and hydroarylation of styrenes have been successfully developed in the presence of isatins or heterocyclic aryl compounds such as benzothiophenes and benzofurans. The reactions tolerate a variety of functional groups and afford the corresponding products in moderate to good yields. Deuterium labeling experiments show that the functionalized hydrogen of styrenes was derived from the nitrogen-hydrogen of the substrates in the hydroamination. Preliminary mechanistic studies suggest that the reactions may be a radical or a carbocation process.
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