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  • 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.

The Journal of organic chemistry (2012-10-11)
Zenghui Lu, Weijian Cui, Siyuan Xia, Yihui Bai, Fang Luo, Gangguo Zhu
ABSTRACT

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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
4-Ethoxymethylene-2-phenyl-2-oxazolin-5-one, purified by recrystallization
Supelco
4-Ethoxymethylene-2-phenyl-2-oxazolin-5-one, analytical standard, for drug analysis