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Minimization of Organocuprate Complexity through Self-Organization: Remarkable Orientation Effect in Mixed Cuprate π Complexes

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  • Rapid Injection NMR in Mechanistic Organocopper Chemistry, part 10. For previous papers in this series, see references [8–15]. We are grateful to the National Science Foundation (USA) for their support of our work through grants 0353061 and 0321056.

Abstract

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They “know” where to go: A powerful orientation effect has been observed in complexes of mixed organocuprates [RTRNTCuLi] and substrates with C[BOND]C, C[BOND]N, and C[BOND]S double bonds (see scheme; Th=thienyl). The preferred geometry of the intermediate complex sets up the facile addition of RT to the double bond, rather than addition of the “dummy ligand”, RNT.

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