Oxidative cross coupling between two nucleophiles has been one of the most popular approaches in chemical synthesis. In recent years, directly employing C-H or X-H as nucleophiles in this transformation, which avoids the use of halides (or halide equivalents) and organometallic reagents, represents green and sustainable chemistry and has attracted more attention. We have focused our attention to utilize phenols as nucleophiles in oxidative cross coupling, which still remains problematic and the selectivity is particularly challenging as phenol could be readily oxidized in the presence of various chemical or biological oxidants.A direct oxidative radical coupling between phenol and olefin was developed to construct dihydrobenzofuran by using FeCl3 as the catalyst and DDQ as the terminal oxidant. Preliminary mechanistic studies revealed that radical was involved in the overall process, DDQ was vital in the initiating step, and meanwhile, FeCl3might act as a Lewis acid to promote this transformation and the high selectivity is due to the Lewis acid.

Iron-catalyzed oxidative radical cross-coupling/cyclization between phenol and olefin

248th National Meeting (2014)

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