Oxidative cyclizations in a nonpolar solvent using molecular oxygen and studies on the stereochemistry of oxypalladation

RM Trend, YK Ramtohul, BM Stoltz

Index: Trend, Raissa M.; Ramtohul, Yeeman K.; Stoltz, Brian M. Journal of the American Chemical Society, 2005 , vol. 127, # 50 p. 17778 - 17788

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Citation Number: 198

Abstract

Oxidative cyclizations of a variety of heteroatom nucleophiles onto unactivated olefins are catalyzed by palladium (II) and pyridine in the presence of molecular oxygen as the sole stoichiometric oxidant in a nonpolar solvent (toluene). Reactivity studies of a number of N- ligated palladium complexes show that chelating ligands slow the reaction. Nearly identical conditions are applicable to five different types of nucleophiles: phenols, primary alcohols, ...