Journal
ORGANIC CHEMISTRY FRONTIERS
Volume 3, Issue 12, Pages 1738-1745Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c6qo00331a
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Funding
- Finnish Cultural Foundation
- Emil Aaltonen Foundation
- Magnus Ehrnrooth Foundation
- Otto Malm Foundation
- Academy of Finland [129062, 289172]
- Academy of Finland (AKA) [129062, 289172, 289172, 129062] Funding Source: Academy of Finland (AKA)
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With an excess of a strong acid, 2,3-dichloro-5,6-dicyano-1,4-quinone (DDQ) is shown to promote metal-free intermolecular oxidative dehydrogenative (ODH) 3,3'-coupling of 2-aryl-benzo[b]furans and 2-aryl-benzo[b]thiophenes up to 92% yield as demonstrated with 9 substrates. Based on the analysis of oxidation potentials and molecular orbitals combined with EPR, NMR and UV-Vis observations, the studied reaction is initiated by a DDQ-substrate charge transfer complex and presumably proceeds via oxidation of the substrate into an electrophilic radical cation that further reacts with another molecule of a neutral substrate. The coupling reactivity can easily be predicted from the oxidation potential of the substrate and the morphology of its frontier molecular orbitals. The intermolecular ODH coupling reaction allowed a concise total synthesis of the natural product shandougenine B.
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