Palladium-catalyzed direct C-H silylation and germanylation of benzamides and carboxamides

Kyalo Stephen Kanyiva, Yoichiro Kuninobu, Motomu Kanai

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78 Citations (Scopus)

Abstract

A palladium-catalyzed regioselective activation of C(sp2)-H and C(sp3)-H bonds of benzamides and carboxamides, followed by coupling with disilanes to afford organosilanes in moderate to high yields, with the aid of 8-aminoquinoline as a directing group, is reported. Catalytic C(sp 2)-H germanylation of benzamides also proceeds under the same palladium catalysis. The reaction tolerates a wide variety of functional groups and is scalable without yield reduction. The bidentate directing group is readily removed and recovered by the reaction with a hydrazine, with concominant generation of an acyl hydrazide.

Original languageEnglish
Pages (from-to)1968-1971
Number of pages4
JournalOrganic Letters
Volume16
Issue number7
DOIs
Publication statusPublished - Apr 4 2014
Externally publishedYes

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All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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