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Palladium‐Catalyzed Isocyanide Insertion with Allylic Esters: Synthesis of N ‐(But‐2‐enoyl)‐ N ‐( tert ‐butyl)benzamide Derivatives via Intramolecular Acyl Transfer Termination
Author(s) -
Chen Si,
Wei WanXu,
Wang Jia,
Xia Yu,
Shen Yi,
Wu XinXing,
Jing Huanwang,
Liang YongMin
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201700765
Subject(s) - chemistry , intramolecular force , benzamide , isocyanide , palladium , allylic rearrangement , imide , medicinal chemistry , catalysis , nitrogen atom , stereochemistry , polymer chemistry , organic chemistry , ring (chemistry)
A novel and unprecedented intramolecular acyl transfer reaction via the palladium‐catalyzed insertion of isocyanide has been established. Isocyanides were inserted into C−O bond under mild conditions, using the readily available allyl ester as the starting materials. In addition, the intramolecular acyl transfer from the ester group oxygen atom to the isocyanide nitrogen atom afforded imide derivatives in moderate to excellent yields. Additionally, this transformation was validated as having operationally simple conditions and excellent functional group compatibility.