Previous studies in the Wolfe lab have demonstrated the utility of Pd-catalyzed alkene difunctionalization reactions for the production of functionalized carbocycles in high yields with excellent stereoselectivity.  These reactions effect the coupling of an aryl or alkenyl triflate containing a pendant alkene with an amine nucleophile using a Pd(0)-catalyst to generate aminocyclopentane products, with formation of two new bonds and one ring.  This presentation will describe an expansion of scope that allows the use of heteroarenes as carbon nucleophiles in these transformations, which form two carbon-carbon bonds in an <i>anti</i>-addition to the unactivated alkene.  Reactions of unprotected NH indole and pyrrole nucleophiles provide carbocycles bearing 3-indolyl or 3-pyrrolyl substituents in good yields with &gt;20:1 dr, with complete selectivity for C-alkylation rather than N-alkylation.  These transformations give straightforward access to substituted heterocycles that are difficult to synthesize using existing methods.<br/>

Palladium-catalyzed alkene difunctionalization reactions of heteroaromatic nucleophiles

254th National Meeting (2017)

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