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. 2024 Aug 12;63(33):e202406936.
doi: 10.1002/anie.202406936. Epub 2024 Jun 30.

Gold-Catalyzed Arylative Cope Rearrangement

Bidisha Paroi  1 , Chayanika Pegu  1 , Manoj V Mane  2 , Nitin T Patil  1
Affiliations

Gold-Catalyzed Arylative Cope Rearrangement

Bidisha Paroi et al. Angew Chem Int Ed Engl. .

Abstract

Cope rearrangements have garnered significant attention owing to their ability to undergo structural reorganization in stereoselective manner. While substantial advances have been achieved over decades, these rearrangements remained applicable exclusively to parent 1,5-hexadienes. Herein, we disclose the gold-catalyzed arylative Cope rearrangement of 1,6-heptadienes via a cyclization-induced [3,3]-rearrangement employing ligand-enabled gold redox catalysis. Detailed mechanistic investigations including several control experiments, cross-over experiment, HRMS analysis, 31P NMR and DFT studies have been performed to underpin the mechanism.

Keywords: Cope rearrangement; cross-coupling; gold catalysis; redox catalysis; π-activation.

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References

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