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Palladium-mediated cyclization of 6-methyl-1-phenyl-6-hepten-2-one to form 3-methyldiphenylmethane: Carbonyl activation by a neutral palladium(II) complex

Publication ,  Journal Article
Han, X; Widenhoefer, RA
Published in: Organometallics
July 30, 2007
Published version (DOI)

Reaction of 6-methyl-1-phenyl-6-hepten-2-one (4) with a stoichiometric mixture of PdCl 2(CH 3CN) 2 (2) and Me 3SiCl in dioxane at 70 °C formed 3-methyldiphenylmethane (6) in 78% isolated yield. A number of experiments supported a mechanism for the conversion of 4 to 6 initiated by palladium-mediated carbonyl-ene reaction to form the isolable palladium alkene-alcohol complex Pd[η 3-HOC(Bn) CH 2C(Me)=CHCH 2CH 2]Cl 2 (7) followed by Me 3SiCl-mediated dehydration to form the unobserved palladium diene complex Pd[η 4-C(Bn)=C(Me)CH=CHCH 2CH 2]Cl 2 (II) and palladium-mediated oxidation of II to form 6. © 2007 American Chemical Society.

Duke Scholars

Ross A. Widenhoefer
Author Ross A. Widenhoefer Chemistry

Published In

Organometallics

DOI

10.1021/om700379g

ISSN

0276-7333

Publication Date

July 30, 2007

Volume

26

Issue

16

Start / End Page

4061 / 4065

Related Subject Headings

  • Organic Chemistry
  • 3406 Physical chemistry
  • 3402 Inorganic chemistry
  • 0399 Other Chemical Sciences
  • 0305 Organic Chemistry
  • 0302 Inorganic Chemistry
 

Citation

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MLA
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Han, X., & Widenhoefer, R. A. (2007). Palladium-mediated cyclization of 6-methyl-1-phenyl-6-hepten-2-one to form 3-methyldiphenylmethane: Carbonyl activation by a neutral palladium(II) complex. Organometallics, 26(16), 4061–4065. https://doi.org/10.1021/om700379g
Han, X., and R. A. Widenhoefer. “Palladium-mediated cyclization of 6-methyl-1-phenyl-6-hepten-2-one to form 3-methyldiphenylmethane: Carbonyl activation by a neutral palladium(II) complex.” Organometallics 26, no. 16 (July 30, 2007): 4061–65. https://doi.org/10.1021/om700379g.
Han, X., and R. A. Widenhoefer. “Palladium-mediated cyclization of 6-methyl-1-phenyl-6-hepten-2-one to form 3-methyldiphenylmethane: Carbonyl activation by a neutral palladium(II) complex.” Organometallics, vol. 26, no. 16, July 2007, pp. 4061–65. Scopus, doi:10.1021/om700379g.
Journal cover image

Published In

Organometallics

DOI

10.1021/om700379g

ISSN

0276-7333

Publication Date

July 30, 2007

Volume

26

Issue

16

Start / End Page

4061 / 4065

Related Subject Headings

  • Organic Chemistry
  • 3406 Physical chemistry
  • 3402 Inorganic chemistry
  • 0399 Other Chemical Sciences
  • 0305 Organic Chemistry
  • 0302 Inorganic Chemistry