Scandium-Catalyzed Benzylic C(sp3)−H Alkenylation of Tertiary Anilines with Alkynes
Xian Xu, Qianlin Sun, and Xin Xu*（徐信）
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, Jiangsu，215123, P. R. China
Org. Lett. 2022, 24, 3970--3975
This work describes the chemo- and stereoselective benzylic C(sp3)–H alkenylation of tertiary ortho-methyl anilines with internal alkynes using a simple β-diketiminato scandium catalyst. This protocol offers an efficient method for the synthesis of a new family of tertiary ortho-allylanilines in high yields. The resultant alkenylation products facilely underwent further chemical transformation to other valuable anilines. A cationic scandium benzyl species was isolated from a stoichiometric reaction and confirmed to be the catalytic intermediate.
链接：//pubs.acs.org/doi/10.1021/acs.orglett.2c01329
