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pH-Controlled Intramolecular Decarboxylative Cyclization of Biarylacetic Acids: Implication on Umpolung Reactivity of Aroyl Radicals

Joydev K. Laha*, Upma Gulati, Saima, Tim Schulte and Martin Breugst*

*NIPER, S. A. S. Nagar, Punjab 160062, India; TU Chemnitz, 09111 Chemnitz, Germany, Email:,

J. K. Laha, U. Gulati, Saima, T. Schulte, M. Breugst, J. Org. Chem., 2022, 87, 6638-6656.

DOI: 10.1021/acs.joc.2c00295

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A pH-controlled polarity umpolung strategy enables a simple intramolecular aroylation of electron-rich arenes under mild conditions to provide different fluorenones, which are important building blocks for biological applications. Unlike previous acylation reactions involving nucleophilic aroyl radicals, this approach likely relies on in situ generated electrophilic aroyl radicals.

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proposed mechanism

Key Words

fluorenones, potassium peroxydisulfate

ID: J42-Y2022