Journal
CHEMISTRY-AN ASIAN JOURNAL
Volume 11, Issue 11, Pages 1664-1667Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.201600193
Keywords
heterocycles; iminoisoindolinone derivatives; nickel-catalyzed; oxidative C-H/N-H isocyanide insertion; oxidative cross-couplings
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Funding
- 973 Program [2011CB808600, 2012CB725302]
- National Natural Science Foundation of China [21390400, 21025206, 21272180, 21302148]
- Research Fund for the Doctoral Program of Higher Education of China [20120141130002]
- Program for ChangJiang Scholars and Innovative Research Team in University [IRT1030]
- Program of Introducing Talents of Discipline to Universities of China (111Program)
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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 pre-functionalization 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.
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