Organolanthanide-catalyzed carbon-heteroatom bond formation. Observations on the facile, regiospecific cyclization of aminoalkynes

Yanwu Li, Peng Fei Fu, Tobin J Marks

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135 Citations (Scopus)

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
Pages (from-to)439-440
Number of pages2
JournalOrganometallics
Volume13
Issue number2
Publication statusPublished - 1994

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ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry

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