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

Stephen Kyalo Kanyiva, Yoichiro Kuninobu, Motomu Kanai

Research output: Contribution to journalArticle

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 - 2014 Apr 4
Externally publishedYes

Fingerprint

Benzamides
hydrazine
Palladium
palladium
Catalysis
Functional groups
hydrazides
Chemical activation
hydrazines
catalysis
activation

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Palladium-catalyzed direct C-H silylation and germanylation of benzamides and carboxamides. / Kanyiva, Stephen Kyalo; Kuninobu, Yoichiro; Kanai, Motomu.

In: Organic Letters, Vol. 16, No. 7, 04.04.2014, p. 1968-1971.

Research output: Contribution to journalArticle

Kanyiva, Stephen Kyalo ; Kuninobu, Yoichiro ; Kanai, Motomu. / Palladium-catalyzed direct C-H silylation and germanylation of benzamides and carboxamides. In: Organic Letters. 2014 ; Vol. 16, No. 7. pp. 1968-1971.
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