Highly selective intramolecular carbene insertion into primary C-H bond of α-diazoacetamides mediated by a (p-cymene)ruthenium(II) carboxylate complex

Vanessa Kar Yan Lo, Zhen Guo, Matthew Kwok Wai Choi, Wing Yiu Yu, Jie Sheng Huang, Chi Ming Che

Research output: Journal article publicationJournal articleAcademic researchpeer-review

53 Citations (Scopus)

Abstract

Complex [(p-cymene)Ru(η1-O2CCF3)2(OH2)] mediated transformation of α-diazoacetamides ArCH2N(C(CH3)3)C(O)CHN2to result in carbene insertion into the primary C-H bond exclusively, with the γ-lactam products being isolated in up to 98% yield. This unexpected reaction is striking in view of the presence of usually more reactive sites such as secondary C-H bonds in the substrates. DFT calculations based on proposed Ru-carbene species provide insight into this unique selectivity.
Original languageEnglish
Pages (from-to)7588-7591
Number of pages4
JournalJournal of the American Chemical Society
Volume134
Issue number18
DOIs
Publication statusPublished - 9 May 2012

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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