Pd-Catalyzed C–S Activation/Isocyanide Insertion/Hydrogenation Enables a Selective Aerobic Oxidation/Cyclization

Pd-Catalyzed C–S Activation/Isocyanide Insertion/Hydrogenation Enables a Selective Aerobic Oxidation/Cyclization

Unique imidoylation of thioorganics with isocyanides endows an unprecedented aerobic oxidation process. Catalyzed by Pd­(Ph3P)2Cl2 in the presence of Ph3SiH under N2 then upon exposure to air, a wide range of α-acyl ketene dithioacetals react with isocyanides to afford 5-hydroxy-α,β-unsaturated γ-la...

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Veröffentlicht in:Organic letters 2016-08, Vol.18 (16), p.3984-3987
Hauptverfasser: Chang, Jian, Liu, Bangyu, Yang, Yang, Wang, Mang
Format: Artikel
Sprache:eng
Schlagworte:
air
catalytic activity
chemical bonding
chemical structure
hydrogenation
Lewis bases
migratory behavior
nitrogen
organic compounds
oxidation
palladium
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Beschreibung
Zusammenfassung:Unique imidoylation of thioorganics with isocyanides endows an unprecedented aerobic oxidation process. Catalyzed by Pd­(Ph3P)2Cl2 in the presence of Ph3SiH under N2 then upon exposure to air, a wide range of α-acyl ketene dithioacetals react with isocyanides to afford 5-hydroxy-α,β-unsaturated γ-lactams via a C–S bond activation, isocyanide migratory insertion, hydrogenation, selective aerobic oxidation, and intramolecular nucleophilic addition sequence.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.6b01780