Synthesis of Cyclohexane-Fused Isocoumarins via Cationic Palladium(II)-Catalyzed Cascade Cyclization Reaction of Alkyne-Tethered Carbonyl Compounds Initiated by Intramolecular Oxypalladation of Ester-Substituted Aryl Alkynes

Synthesis of Cyclohexane-Fused Isocoumarins via Cationic Palladium(II)-Catalyzed Cascade Cyclization Reaction of Alkyne-Tethered Carbonyl Compounds Initiated by Intramolecular Oxypalladation of Ester-Substituted Aryl Alkynes

A cationic Pd­(II)-catalyzed cascade cyclization reaction of alkyne-tethered carbonyl compounds was developed. This reaction is initiated by intramolecular oxypalladation of alkynes with an ester group followed by 1,2-addition of the formed C–Pd­(II) bond to the carbonyl group, providing a highly ef...

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Veröffentlicht in:Journal of organic chemistry 2016-04, Vol.81 (8), p.3423-3429
Hauptverfasser: Zhang, Jianbo, Han, Xiuling, Lu, Xiyan
Format: Artikel
Sprache:eng
Schlagworte:
Alkynes - chemistry
Catalysis
Cations - chemistry
Cyclization
Cyclohexanes - chemical synthesis
Cyclohexanes - chemistry
Esters
Indoles - chemistry
Isocoumarins - chemical synthesis
Isocoumarins - chemistry
Molecular Structure
Palladium - chemistry
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Zusammenfassung:A cationic Pd­(II)-catalyzed cascade cyclization reaction of alkyne-tethered carbonyl compounds was developed. This reaction is initiated by intramolecular oxypalladation of alkynes with an ester group followed by 1,2-addition of the formed C–Pd­(II) bond to the carbonyl group, providing a highly efficient method for the synthesis of cyclohexane-fused isocoumarins.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b00128