Pd-Catalyzed Semmler–Wolff Reactions for the
Conversion of Substituted Cyclohexenone Oximes to Primary Anilines
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Abstract
Homogeneous Pd catalysts have been
identified for the conversion
of cyclohexenone and tetralone <i>O-</i>pivaloyl oximes
to the corresponding primary anilines and 1-aminonaphthalenes. This
method is inspired by the Semmler–Wolff reaction, a classic
method that exhibits limited synthetic utility owing to its forcing
conditions, narrow scope, and low product yields. The oxime N–O
bond undergoes oxidative addition to Pd<sup>0</sup>(PCy<sub>3</sub>)<sub>2</sub>, and the product of this step has been characterized
by X-ray crystallography and shown to undergo dehydrogenation to afford
the aniline product
