Intramolecular Pd-mediated processes of amino-tethered aryl halides and ketones: Insight into the ketone α-arylation and carbonyl-addition dichotomy. A new class of …

D Solé, L Vallverdú, X Solans…

Index: Sole, Daniel; Vallverdu, Lluis; Solans, Xavier; Font-Bardia, Merce; Bonjoch, Josep Journal of the American Chemical Society, 2003 , vol. 125, # 6 p. 1587 - 1594

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Citation Number: 112

Abstract

An exploration of the scope and limitations of Pd (0)-catalyzed intramolecular coupling reactions of amino-tethered aryl halides and ketones has been conducted. Two different and competitive reaction pathways starting from ω-(2-haloanilino) alkanones, enolate arylation and addition to the carbonyl group, have been observed, while ω-(2-halobenzylamino) alkanones exclusively underwent the enolate arylation process. The dichotomy between ...