It has been previously shown that both ?1 s- and ?3 p-allylcopper(III) intermediates can be observed in the S-N-2 and S-N-2' reactions of organocuprate(I) reagents with allylic acetates and chlorides. In accord with these results, we have now shown that the reaction of Me-2-CuLi�LiI with benzalacetone 1 followed by the addition of chlorotriethylsilane affords an ?3 p-allylcopper(III) intermediate, 2. This previously unseen allylic intermediate has been postulated to be operative in conjugate addition reactions, but now by using the rapid injection nuclear magnetic resonance technique, this intermediate has been observed and characterized at low temperature for the first time.                                                                      

Identification and characterization of an η<sup>3</sup> π-allylcopper(III) intermediate in the conjugate addition reaction

241st National Meeting (2011)

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