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Gold(I)-Catalyzed Synthesis of Heterocycles via Allene Oxide from Propargylic Alcohols

Nabakumar Bera, Bhabani Sankar Lenka, Sangita Bishi, Shantanu Samanta and Debayan Sarkar*

*Department of Chemistry, Indian Institute of Technology, Indore, Madhya Pradesh 453552, India, Email:

N. Bera, B. S. Lenka, S. Bishi, S. Samanta, B. Sarkar, J. Org. Chem., 2022, 87, 9729-9754.

DOI: 10.1021/acs.joc.2c00780

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Gold(I) catalysis enables an efficient synthesis of N-protected pyrroles and 5,6-dihydropyridin-3(4H)-ones from N-protected and unprotected 5-aminopent-2-yn-1-ol, respectively. Atom-economic syntheses of hydroxyalkyl indoles and benzofurans are also described. The methods offer short reaction time, low catalyst loading, high yield, and simple open-flask reaction conditions.

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Key Words

pyrroles, indoles, benzofurans

ID: J42-Y2022