Pd-catalyzed Semmler-Wolff reactions for the conversion of substituted cyclohexenone oximes to primary anilines
Homogeneous Pd catalysts have been identified for the conversion of cyclohexenone and tetralone O-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 Pd0(PCy3)2, and the product of this step has been characterized by X-ray crystallography and shown to undergo dehydrogenation to afford the aniline product.
Hong, Wan Pyo,Iosub, Andrei V.,Stahl, Shannon S.
supporting information
p. 13664 - 13667
(2013/10/01)
Application of Semmler-Wolff Reaction for the Synthesis of 2-Aminobiphenyls
Semmler-Wolff reaction of 1-hydroxyimino-2-aryl-2-cyclohexenes (I) yields the corresponding 2-aminobiphenyls (II) in 40-55percent yield.The 2-aminobiphenyls have been fully characterized through spectral data.Further confirmation of the structures of 2-aminobiphenyls is obtained by their conversion to the corresponding phenanthridine derivatives (IV).
Sivasubramanian, S.,Muthusubramanian, S.,Ramasamy, S.,Arumugam, N
p. 552 - 554
(2007/10/02)
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