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Palladium‐Catalyzed Imidoylative Cyclization of α‐Isocyanoacetamides: Efficient Access to C2‐Diversified Oxazoles
Author(s) -
Wang Jian,
Luo Shuang,
Huang Jinbo,
Mao Tingting,
Zhu Qiang
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201403033
Subject(s) - palladium , isocyanide , aryl , catalysis , halide , chemistry , alkyl , cascade , combinatorial chemistry , migratory insertion , medicinal chemistry , organic chemistry , chromatography
A novel procedure for the synthesis of C2‐diversified oxazoles, through palladium‐catalyzed imidoylative cyclization of α‐isocyanoacetamides with aryl, vinyl, alkynyl halides, or triflates, was developed. Migratory insertion of isocyanide into a C sp 3‐palladium(II) intermediate in a cascade process was also realized, generating alkyl‐substituted oxazoles. Therefore, oxazoles functionalized at the C2 position with sp, sp 2 , and sp 3 hybridized carbon atoms are accessible by applying this method.