Direct Cross‐Couplings of Propargylic Diols |
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Authors: | Dr. Nicholas J. Green Dr. Anthony C. Willis Prof. Dr. Michael S. Sherburn |
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Affiliation: | Research School of Chemistry, Australian National University, Canberra, ACT, Australia |
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Abstract: | [Pd(PPh3)4] catalyzes a Suzuki–Miyaura‐like twofold cross‐coupling sequence between underivatized propargylic diols and either aryl or alkenyl boronic acids to furnish highly substituted 1,3‐dienes. Thus, 2,3‐diaryl‐1,3‐butadienes and their dialkenic congeners ([4]dendralenes) are delivered in a (pseudo)halogen‐free, single‐step synthesis which supersedes existing methods. Allenols are also readily formed. Treatment of these single‐ and twofold cross‐coupled products with acid leads to remarkably short syntheses of highly‐substituted benzofulvenes and aryl indenes, respectively. |
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Keywords: | alkenes allenes cross-coupling palladium synthetic methods |
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