Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 140, Issue 36, Pages 11202-11205Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.8b07578
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Funding
- Ohio State University
- National Institutes of Health [NIH R35 GM119812]
- National Science Foundation [NSF CAREER 1654656]
- American Chemical Society Petroleum Research Fund
- HHMI Gilliam Fellowship
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R35GM119812] Funding Source: NIH RePORTER
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The first catalytic strategy to harness imidate radicals has been developed. This approach enables alkene difunctionalization of allyl alcohols by photocatalytic reduction of their oxime imidates. The ensuing imidate radicals undergo consecutive intra- and intermolecular reactions to afford (i) hydroamination, (ii) aminoalkylation, or (iii) aminoarylation, via three distinct radical mechanisms. The broad scope and utility of this catalytic method for imidate radical reactivity is presented, along with comparisons to other N-centered radicals and complementary, closed-shell imidate pathways.
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