Abstract

Switchable reaction: Reagent-dependent regioselective additions to dual-activated alkynes have been developed (see scheme; E=electrophile, R1=alkyl, R2=alkyl or aryl). The reaction with an alkyl radical afforded the β-addition product, whereas the reaction with an organocuprate gave the α-adduct with high regio- and stereoselectivities. These reactions were applied to domino and one-pot reactions, providing tetrasubstituted and functionalized alkenes. Computational studies have been used to rationalize the selectivity.

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