Concepedia

Dienyl Homoallyl Alcohols via Palladium Catalyzed Ene-Type Reaction of Aldehydes with 1,3-Dienes

Masahiro Fukushima, Daiki Takushima, Masanari Kimura

Journal of the American Chemical Society · 2010 · 34 citations · 39 references

DOI

Concepts

Abstract

The combination of Pd catalyst and Xantphos ligand in the presence of Et(3)B nicely promotes the allylation of aldehydes with conjugated dienes to provide dienyl homoallyl alcohols in excellent yields. The reaction occurs selectively at the C-C double bond bearing higher electron density.

References

39

Pd-Catalyzed Intermolecular Amidation of Aryl Halides:  The Discovery that Xantphos Can Be Trans-Chelating in a Palladium Complex

Jingjun Yin, Stephen L. Buchwald · Journal of the American Chemical Society · 2002 · 468 citations

, , +16

Facile Ar−CF<sub>3</sub> Bond Formation at Pd. Strikingly Different Outcomes of Reductive Elimination from [(Ph<sub>3</sub>P)<sub>2</sub>Pd(CF<sub>3</sub>)Ph] and [(Xantphos)Pd(CF<sub>3</sub>)Ph]

Vladimir V. Grushin, William Marshall · Journal of the American Chemical Society · 2006 · 320 citations

, , +11

Mechanisms of 1,1-reductive elimination from palladium

Arlene L. Gillie, J. K. Stille · Journal of the American Chemical Society · 1980 · 313 citations

, , +6

A Highly Active Palladium Catalyst for Intermolecular Hydroamination. Factors that Control Reactivity and Additions of Functionalized Anilines to Dienes and Vinylarenes

Adam M. Johns, Masaru Utsunomiya, Christopher D. Incarvito et al. · Journal of the American Chemical Society · 2006 · 309 citations

, , +16

Ruthenium-Catalyzed C−C Bond Forming Transfer Hydrogenation: Carbonyl Allylation from the Alcohol or Aldehyde Oxidation Level Employing Acyclic 1,3-Dienes as Surrogates to Preformed Allyl Metal Reagents

Fumitoshi Shibahara, John F. Bower, Michael J. Krische · Journal of the American Chemical Society · 2008 · 199 citations · Full text

, , +13