Development of an anomalous Heck reaction: skeletal rearrangement of divinyl and enyne carbinols |
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Authors: | Ndungu J Maina Larson Kimberly K Sarpong Richmond |
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Institution: | Department of Chemistry, University of California, Berkeley, California 94720, USA. |
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Abstract: | reaction: see text] A general set of conditions that achieves the union of aryl halides and divinyl or enyne carbinols to afford tri- or tetrasubstituted olefins in good yields (up to 83%) is described. The mechanism by which this proceeds is believed to involve the intermediacy of a cyclopropanol, followed by a novel skeletal reorganization. The ability to suppress beta-hydride elimination of organopalladium intermediates appears to be critical to the success of these processes. |
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