Transition-metal-catalyzed C-C bond formation via C-H activation. Intermolecular hydroacylation: The addition of aldehydes to alkenes

Todd B. Marder, D. Christopher Roe, David Milstein

Research output: Contribution to journalArticle

176 Citations (Scopus)

Abstract

The indenyl complex [(η5-C9H7)Rh(η2-C 2H4)2] (1) is a catalyst for intermolecular hydroacylation, the addition of aldehydes to alkenes. Aldehyde decarbonylation is not a significant process with aromatic aldehydes and 1. The model system PhCHO + C2H4 gives propiophenone cleanly with turnover rates of up to ca. 4 h-1 at 100°C and 1000 psi charge of C2H4. Deuterium-labeling studies were conducted by in situ 2H NMR spectroscopy under catalytic conditions using a specially designed high-pressure NMR tube. Other aldehydes and formates also add to ethylene using 1.

Original languageEnglish
Pages (from-to)1451-1453
Number of pages3
JournalOrganometallics
Volume7
Issue number6
Publication statusPublished - 1988

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Alkenes
aldehydes
Aldehydes
alkenes
Transition metals
Chemical activation
transition metals
activation
Propiophenones
Formates
nuclear magnetic resonance
Deuterium
formates
Labeling
Nuclear magnetic resonance spectroscopy
marking
deuterium
ethylene
Nuclear magnetic resonance
tubes

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry

Cite this

Transition-metal-catalyzed C-C bond formation via C-H activation. Intermolecular hydroacylation : The addition of aldehydes to alkenes. / Marder, Todd B.; Roe, D. Christopher; Milstein, David.

In: Organometallics, Vol. 7, No. 6, 1988, p. 1451-1453.

Research output: Contribution to journalArticle

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