Leveraging the Persistent Radical Effect in the Synthesis of trans-2,3-Diaryl Dihydrobenzofurans** |
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| Authors: | Bec J. Roldan Travis A. Hammerstad Matthew S. Galliher Mitchell H. Keylor Prof. Dr. Derek A. Pratt Prof. Dr. Corey R. J. Stephenson |
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| Affiliation: | 1. Department of Chemistry, University of Michigan, Ann Arbor, 930 N University Ave, Ann Arbor, MI 48109 USA;2. Department of Chemistry and Biomolecular Sciences, University of Ottawa, Ottawa, Ontario, K1N 6N5 Canada |
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| Abstract: | A simple method for accessing trans-2,3-diaryl dihydrobenzofurans is reported. This approach leverages the equilibrium between quinone methide dimers and their persistent radicals. This equilibrium is disrupted by phenols that yield comparatively transient phenoxyl radicals, leading to cross-coupling between the persistent and transient radicals. The resultant quinone methides with pendant phenols rapidly cyclize to form dihydrobenzofurans (DHBs). This putative biomimetic access to dihydrobenzofurans provides superb functional group tolerance and a unified approach for the synthesis of resveratrol-based natural products. |
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| Keywords: | Antioxidants Dihydrobenzofuran Quinone Methides Radicals Resveratrol |
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