Scandium-Catalyzed para-Selective Alkylation of Aromatic Amines with Alkenes
Jianhong Su, Yanping Cai, and Xin Xu*（徐信）
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, P. R. China
Org. Lett.2019, 21, 9055--9059
An efficient para-alkylation of primary and secondary anilines with a variety of sterically encumbered alkenes using a simple β-diketiminato scandium catalyst is reported. This protocol features 100% atom economy, excellent chemo- and regioselectivity, broad substrate scope, and good functional group tolerance. Mechanistic studies disclosed that the reaction probably proceeded via a tandem hydroamination/Hofmann–Martius rearrangement.