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Catalytic Alkene Difunctionalization via Imidate Radicals.

ABSTRACT: 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.

SUBMITTER: Nakafuku KM

PROVIDER: S-EPMC6519729 | biostudies-literature | 2018 Sep

REPOSITORIES: biostudies-literature

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Catalytic Alkene Difunctionalization via Imidate Radicals.

Nakafuku Kohki M KM Fosu Stacy C SC Nagib David A DA

Journal of the American Chemical Society 20180829 36

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, alon ...[more]

PMID: 30156404

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