Cationic lr(l)-catalyzed sp3 C- H bond alkenylation of amides with alkynes

Kyoji Tsuchikama, Mitsugu Kasagawa, Kohei Endo, Takanori Shibata*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

104 Citations (Scopus)


A cationic lr(l)-BINAP catalyst cleaved sp3 C-H bonds of arylamides rather than sp2 C-H bonds, which was followed by alkenylation with alkynes to give allylamides. Several types of amides and alkynes were suitable as substrates, and the corresponding allylamides were obtained in moderate to good yield. We also demonstrated that carbonyl-directed sp3 C-H bond cleavage would be an initial step in the present reaction by a deuterium-labeling experiment.

Original languageEnglish
Pages (from-to)1821-1823
Number of pages3
JournalOrganic Letters
Issue number8
Publication statusPublished - 2009 Apr 16

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry


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