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Dual Role of Oxoaldehydes: Divergent Synthesis of 3-Aryl- and 3-Aroylcoumarins

Ali Moazzam, Meysam Khodadadi, Farnaz Jafarpour* and Mehdi Ghandi

*School of Chemistry, College of Science, University of Tehran, P.O. Box 14155-6619 Tehran, Iran, Email:

A. Moazzam, M. Khodadadi, F. Jafarpour, M. Ghandi, J. Org. Chem., 2022, 87, 3630-3637.

DOI: 10.1021/acs.joc.1c02159

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A simple switch in reaction conditions enables facile and efficient syntheses of various valuable 3-aryl- and 3-aroylcoumarins by direct arylation and aroylation of coumarins with glyoxals in a metal-free manner. This approach accommodates a broad substrate scope and high yields of the two types of cross-coupling reactions starting from identical starting materials.

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proposed mechanism

Key Words

coumarins, DTBP, TBHP

ID: J42-Y2022