Hydrocarbamoylation of Unsaturated Bonds by Nickel/Lewis-Acid Catalysis

Yoshiaki Nakao, Hiroaki Idei, Stephen Kyalo Kanyiva, Tamejiro Hiyama

Research output: Contribution to journalArticle

112 Citations (Scopus)

Abstract

Formamides are found to undergo addition reactions across alkynes and 1,3-dienes by nickel/Lewis acid catalysis to give a variety of α, β- and β,γ-unsaturated amides with stereo- and regioselectivity. Intramolecular insertion reactions of olefins into the C-H bonds of formamides also proceed under similar conditions. The presence of Lewis acid cocatalysts is crucial, and formamide coordination to the Lewis acid is considered to be responsible for the activation of their formyl C-H bonds probably through oxidative addition to nickel(0).

Original languageEnglish
Pages (from-to)5070-5071
Number of pages2
JournalJournal of the American Chemical Society
Volume131
Issue number14
DOIs
Publication statusPublished - 2009 Apr 15
Externally publishedYes

Fingerprint

Lewis Acids
Formamides
Nickel
Catalysis
Acids
Stereoselectivity
Regioselectivity
Addition reactions
Alkynes
Alkenes
Amides
Olefins
Chemical activation

ASJC Scopus subject areas

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

Cite this

Hydrocarbamoylation of Unsaturated Bonds by Nickel/Lewis-Acid Catalysis. / Nakao, Yoshiaki; Idei, Hiroaki; Kanyiva, Stephen Kyalo; Hiyama, Tamejiro.

In: Journal of the American Chemical Society, Vol. 131, No. 14, 15.04.2009, p. 5070-5071.

Research output: Contribution to journalArticle

Nakao, Yoshiaki ; Idei, Hiroaki ; Kanyiva, Stephen Kyalo ; Hiyama, Tamejiro. / Hydrocarbamoylation of Unsaturated Bonds by Nickel/Lewis-Acid Catalysis. In: Journal of the American Chemical Society. 2009 ; Vol. 131, No. 14. pp. 5070-5071.
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