The organolanthanide complex (η5-Me5C5)2-SmCH(TMS)2 serves as a precatalyst for the efficient and regiospecific hydroamination/cyclization of aliphatic and aromatic aminoalkynes RC≡C(CH2)nNH2 to yield the corresponding heterocycles RCH2C=N(CH2)n-1CH2. Kinetic and mechanistic evidence argues that the turnover-limiting step is intramolecular alkyne insertion into the Sm—N bond followed by rapid protonolysis of the resulting Sm—C bond.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry