Journal
TETRAHEDRON
Volume 131, Issue -, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2022.133228
Keywords
Alkene difunctionalization; Cyano migration; Photochemistry; Radical reactions; Desaturation
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We describe a novel reaction mode involving functional group migration, which is utilized for the radical-mediated remote desaturation of hexenenitriles. The reaction proceeds through consecutive alkene sulfonylation, intramolecular cyano migration, and single-electron oxidation of benzyl radical to cation followed by deprotonation, resulting in various densely functionalized alkenes. The protocol offers mild photocatalytic conditions, broad functional group tolerance, and high product diversity.
We report a new reaction mode involving functional group migration, which is applied to the radical -mediated remote desaturation of hexenenitriles. The reaction proceeds through consecutive alkene sulfonylation, intramolecular cyano migration, and single-electron oxidation of benzyl radical to cation followed by deprotonation, leading to a variety of densely functionalized alkenes. The protocol features mild photocatalytic conditions, broad functional group tolerance, and high product diversity.(c) 2022 Elsevier Ltd. All rights reserved.
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