Preparation of 3,4,5-Trisubstituted Oxazolones by Pd-Catalyzed Coupling of N‑Alkynyl tert-Butyloxycarbamates with Aryl Halides and Related Electrophiles

Preparation of 3,4,5-Trisubstituted Oxazolones by Pd-Catalyzed Coupling of N‑Alkynyl tert-Butyloxycarbamates with Aryl Halides and Related Electrophiles

A novel palladium-catalyzed approach for the assembly of 3,4,5-trisubstituted oxazolones has been achieved by the coupling of N-alkynyl tert-butyloxycarbamates with aryl halides and related electrophiles, which involves an oxidative addition followed by oxypalladation/reductive elimination. The reac...

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Veröffentlicht in:Journal of organic chemistry 2012-11, Vol.77 (21), p.9871-9877
Hauptverfasser: Lu, Zenghui, Cui, Weijian, Xia, Siyuan, Bai, Yihui, Luo, Fang, Zhu, Gangguo
Format: Artikel
Sprache:eng
Schlagworte:
Catalysis
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Hydrocarbons, Halogenated - chemistry
Magnetic Resonance Spectroscopy
Molecular Structure
Organic chemistry
Oxazolone - chemistry
Palladium - chemistry
Preparations and properties
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Zusammenfassung:A novel palladium-catalyzed approach for the assembly of 3,4,5-trisubstituted oxazolones has been achieved by the coupling of N-alkynyl tert-butyloxycarbamates with aryl halides and related electrophiles, which involves an oxidative addition followed by oxypalladation/reductive elimination. The reaction provides a convenient access to diversely substituted oxazolones in satisfactory yields and shows good functional group compatibility.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo301794w