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Diphenyl-Diselenide-Mediated Domino Claisen-Type Rearrangement/Cyclization of Propargylic Aryl Ethers: Synthesis of Naphthofuran-2-carboxaldehyde Derivatives.

Jun-Dan FangXiao-Biao YanWu-Jie LinYi-Chuan ZhaoXue-Yuan Liu
Published in: Organic letters (2019)
A diphenyl-diselenide-mediated Claisen-type rearrangement/cyclization of propargylic aryl ethers under metal-free conditions is developed, affording various naphthofuran-2-carboxaldehydes in moderate to excellent yield. The broad substrate scope and excellent functional group compatibility suggest that it can be a straightforward and powerful method to access naphthofuran-2-carboxaldehydes in a highly regioselective manner. Moreover, this reaction can be scaled up to the gram scale.
Keyphrases
  • gram negative