Control of Chemo-, Regio-, and Stereoselectivities in Ligand-Free Pd-Catalyzed Oxidative Heck Reactions of Arylboronic Acids or Alkenylboronate with Allyl Esters
Organic Letters2009Vol. 11(14), pp. 2980–2983
Citations Over TimeTop 10% of 2009 papers
Abstract
A ligand-free Pd-catalyzed highly selective oxidative Heck reaction of organoboronic acids with allyl esters was developed. Beta-H elimination is highly chemoselectively controlled, leading to gamma-substituted allyl esters, which is contrary to the traditional Heck-type reactions of allyl esters. Moreover, the regio- and stereoselectivities are also high due to the chelation between O and Pd atoms.
Related Papers
- → Metallic Palladium in the Heck Reaction: Active Catalyst or Convenient Precursor?(2001)197 cited
- → Preparation, Structure, and Reactions of Trifluoroacetimidoyl Palladium(II) Complexes(2011)17 cited
- → Preparation of organo palladium sols from palladium complexes in various alcohols(1994)32 cited
- → Selectivity in reductive elimination from dialkyl(aryl)palladium(IV) complexes, and the observation of benzyl halide transfer from palladium(IV) to palladium(II). The X‐ray structure of methyl(phenyl)(2,2′‐bipyridyl)palladium(II)(1991)24 cited
- → Metallic Palladium in the Heck Reaction: Active Catalyst or Convenient Precursor?(2001)2 cited