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A novel palladium(0) catalysed tandem 1,3-allyl shift and Heck arylation |
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| Authors: | Stephen P. Watson Graham R. Knox Nicola M. Heron |
| Affiliation: | a Glaxo Research and Development Limited, Ware, Hertfordshire, SG12 0DP, U.K. b Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street Glasgow, G1 1XL, U.K. |
| Abstract: | On treatment with Pd(PPh3)4 allyl vinyl ether (1) undergoes a Pd(0) catalysed 1,3 oxygen to carbon allyl shift to afford -allyl ketone (2). In the presence of both Pd(PPh3)4 and base the allyl vinyl ether undergoes a Pd(0) catalysed tandem 1,3 allyl shift and intramolecular Heck arylation to give the spiro indane (3). Mechanistic investigations suggest that the 1,3-allyl shift proceeds via a π-allyl palladium intermediate. |
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