Organolanthanide-Catalyzed Carbon–Heteroatom Bond Formation. Observations on the Facile, Regiospecific Cyclization of Aminoalkynes

Yanwu Li, Peng Fei Fu, Tobin Jay Marks*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

135 Scopus citations

Abstract

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.

Original languageEnglish (US)
Pages (from-to)439-440
Number of pages2
JournalOrganometallics
Volume13
Issue number2
DOIs
StatePublished - Feb 1 1994

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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