Palladium (0)-catalyzed allylation of highly acidic and nonnucleophilic anilines. The origin of stereochemical scrambling when using allylic carbonates

…, L Morral, R Pleixats

Index: Moreno-Manas, Marcial; Morral, Lurdes; Pleixats, Roser Journal of Organic Chemistry, 1998 , vol. 63, # 18 p. 6160 - 6166

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Citation Number: 57

Abstract

Acidic anilines such as diphenylamine, phenothiazine, and nitroanilines are efficiently allylated under palladium catalysis using allyl carbonates as allylating reagents. A stereochemical study of the reactions of ethyl cis-5-methyl-2-cyclohexenylcarbonate with 4- nitro-and 2, 4-dinitroaniline was performed. Bidentate phosphines as stabilizing ligands gave clean retention of configuration whereas triphenylphosphine permitted cis-trans ...

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