Chelation-controlled, palladium-catalyzed vinylic substitution reactions of vinyl ethers. 2-Arylethanal equivalents from aryl halides

CM Andersson, J Larsson…

Index: Andersson, Carl-Magnus; Larsson, Joakim; Hallberg, Anders Journal of Organic Chemistry, 1990 , vol. 55, # 22 p. 5757 - 5761

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Citation Number: 74

Abstract

The regioselectivity of palladium-catalyzed arylation reactions of a series of nitrogen- containing vinyl ethers is reported. The presence of a@ amino substituent gives a profound influence on regiochemistry. Thus, the arylation of [2-(dimethy1amino) ethoxylethene (IC) with a variety of aryl iodides and bromides provides the fl-arylation products [2-[2- (dimethylamino) ethoxy] ethenyl] arenes (3) with at least 95% selectivity and in good ...