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Pyrenedione-Catalyzed α-Olefination of Nitriles under Visible-Light Photoredox Conditions

Amreen K. Bains, Yadav Ankit and Debashis Adhikari*

*Department of Chemical Sciences, Indian Institute of Science Education and Research (IISER)-Mohali, SAS Nagar, Punjab-140306, India, Email:

A. K. Bains, Y. Ankit, D. Adhikari, Org. Lett., 2021, 23, 2019-2023.

DOI: 10.1021/acs.orglett.1c00162

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A combination of pyrenedione (PD) and KOtBu achieves a facile alcohol dehydrogenation under visible-light excitation in the presence of aerobic oxygen as the terminal oxidant. The resulting carbonyl compounds can be easily converted to vinyl nitriles in a single-pot reaction. This environmentally benign, organocatalytic α-olefination of nitriles operates at low temperature.

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proposed mechanism

Key Words

vinyl nitriles, oxygen, organocatalysis, photochemistry

ID: J54-Y2021