Palladium-catalyzed carbocyclization of alkynyl ketones proceeding through a carbopalladation pathway

Natalia Chernyak, Serge I. Gorelsky, Vladimir Gevorgyan

Research output: Contribution to journalArticle

57 Citations (Scopus)

Abstract

Dig this: 5-exo-dig carbocyclization of 1 into 2 features intramolecular carbopalladation of alkyne with Pd enolate (see scheme). DFT calculations show that the key Pd enolate forms by deprotonation assisted byb PdII acetate. Subsequent intramolecular alkyne carbopalladation, Z-E isomerization of the formed vinyl palladium species, and protiodepalladation leads to E-alkylidene indanones. (Chemical Equation Presented).

Original languageEnglish (US)
Pages (from-to)2342-2345
Number of pages4
JournalAngewandte Chemie - International Edition
Volume50
Issue number10
DOIs
StatePublished - Mar 1 2011
Externally publishedYes

Fingerprint

Deprotonation
Alkynes
Palladium
Isomerization
Ketones
Discrete Fourier transforms
Indans
Acetates

Keywords

  • C-H activation
  • Carbocyclization
  • Computational chemistry
  • Homogeneous catalysis
  • Palladium

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

Palladium-catalyzed carbocyclization of alkynyl ketones proceeding through a carbopalladation pathway. / Chernyak, Natalia; Gorelsky, Serge I.; Gevorgyan, Vladimir.

In: Angewandte Chemie - International Edition, Vol. 50, No. 10, 01.03.2011, p. 2342-2345.

Research output: Contribution to journalArticle

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