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Synthesis of Tetrasubstituted Furans through One-Pot Formal [3 + 2] Cycloaddition Utilizing [1,2]-Phospha-Brook Rearrangement

Azusa Kondoh, Kohei Aita, Sho Ishikawa and Masahiro Terada*

*Department of Chemistry, Graduate School of Science, Tohoku University, Aoba-ku, Sendai 980-8578, Japan, Email:

A. Kondoh, K. Aita, S. Ishikawa, M. Terada, Org. Lett., 2020, 22, 2105-2110.

DOI: 10.1021/acs.orglett.0c00619 (free Supporting Information)

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A [1,2]-phospha-Brook rearrangement under Brønsted base catalysis enables an efficient synthesis of 2,4,5-trisubstituted-3-iodofurans via a formal [3 + 2] cycloaddition of an in situ generated α-oxygenated propargyl anion to an aldehyde and a subsequent intramolecular cyclization mediated by N-iodosuccinimide. The method provides access to a wide range of tetrasubstituted furans.

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proposed reaction pathway

Key Words

furans, Brook rearrangement, NIS

ID: J54-Y2020