Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 359, Issue 7, Pages 1138-1143Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201600925
Keywords
copper; molecular oxygen; oxidation; photochemistry; radicals
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Funding
- Ministry of Science and Technology, Taiwan
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A novel visible light-mediated, copper-catalysed aerobic oxidation of the CC bond in ynamides/ynamines at room temperature by using molecular oxygen as an oxidant is described. Overall, 23 examples were demonstrated with substrates having a wide range of functional groups. The current protocol can be readily scaled up to a preparative (1-2g) scale with high yields (78-92%), high atom efficiency, and reaction mass efficiency. The mechanistic study shows that in-situ formation of a copper(I)-coordinated pi-complex (lambda(max)=460nm) is most probably the key light absorbing species responsible for the visible light-induced oxidation of ynamides and ynamines. This sustainable oxidation approach allows the direct synthesis of potentially important novel alpha-ketoimide/-ketoamide skeletons without the need of external oxidants (organic/inorganic oxidants) and generation of stoichiometric amounts of wastes.
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