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Nickel‐Catalyzed Oxidative C−H/N−H Isocyanide Insertion: An Efficient Synthesis of Iminoisoindolinone Derivatives
Author(s) -
Hao Wenyan,
Tian Jun,
Li Wu,
Shi Renyi,
Huang Zhiliang,
Lei Aiwen
Publication year - 2016
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201600193
Subject(s) - isocyanide , chemistry , nucleophile , catalysis , oxidative phosphorylation , combinatorial chemistry , nickel , insertion reaction , oxidative addition , migratory insertion , transformation (genetics) , medicinal chemistry , stereochemistry , organic chemistry , biochemistry , gene
Transition metal‐catalyzed isocyanide insertion has served as a fundamental and important chemical transformation. Classical isocyanide insertion usually occurs between organohalides and nucleophiles, which normally involves tedious and non‐atom‐economical prefunctionalization processes. However, oxidative C−H/N−H isocyanide insertion offers an efficient and green alternative. Herein, a nickel‐catayzed oxidative C−H/N−H isocyanide insertion of aminoquinoline benzamides has been developed. Different kinds of iminoisoindolinone derivatives could be synthesized in good yields by utilizing Ni(acac) 2 as the catalyst. In this transformation, isocyanide serves as an efficient C1 connector, which further inserted into two simple nucleophiles (C−H/N−H), representing an effective way to construct heterocycles.