Organic letters

Catalytic SN2′-Selective Substitution of Allylic Chlorides With Arylboronic Esters

AM Whittaker, RP Rucker, G Lalic

Index: Whittaker, Aaron M.; Rucker, Richard P.; Lalic, Gojko Organic Letters, 2010 , vol. 12, # 14 p. 3216 - 3218

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Citation Number: 68

Abstract

A copper-catalyzed SN2′-selective arylation of allylic chlorides has been achieved using arylboronic esters as nucleophiles. Arylation products were obtained in high yield with a variety of allylic chlorides and arylboronic esters in the presence of a wide range of functional groups. A mechanism is proposed on the basis of the results of stoichiometric experiments and the isolation of the proposed intermediate.