Examination of the mechanism of Rh2 (II)-catalyzed carbazole formation using intramolecular competition experiments

BJ Stokes, KJ Richert, TG Driver

Index: Stokes, Benjamin J.; Richert, Kathleen J.; Driver, Tom G. Journal of Organic Chemistry, 2009 , vol. 74, # 17 p. 6442 - 6451

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Citation Number: 74

Abstract

The use of a rhodium (II) carboxylate catalyst enables the mild and stereoselective formation of carbazoles from biaryl azides. Intramolecular competition experiments of triaryl azides suggested the source of the selectivity. A primary intramolecular kinetic isotope effect was not observed, and correlation of the product ratios with Hammett σ+ values produced a plot with two intersecting lines with opposite ρ values. These data suggest that electronic ...