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: adhikari
iisermohali.ac.in
A. K. Bains, Y. Ankit, D. Adhikari, Org. Lett., 2021, 23, 2019-2023.
DOI: 10.1021/acs.orglett.1c00162
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Abstract
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
