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Exploiting the Reactivity of Isocyanide: Coupling Reaction between Isocyanide and Toluene Derivatives Using the Isocyano Group as an N1 Synthon

Zhiqiang Liu, Xinglu Zhang, Jianxiong Li, Feng Li, Chunju Li, Xueshun Jia and Jian Li*

*Department of Chemistry, Innovative Drug Research Center, Shanghai University, 99 Shangda Road, Shanghai 200444, P. R. China, Email:

Z. Liu, X. Zhang, J. Li, F. Li, C. Li, X. Jia, J. Li, Org. Lett., 2016, 18, 4032-4035.

DOI: 10.1021/acs.orglett.6b01928 (free Supporting Information)

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In an unusual oxidative coupling reaction of isocyanide and toluene derivatives using tetrabutylammonium iodide (TBAI) as a catalyst, the isocyano group acts formally as an N1 synthon, thus expanding the reactivity profile of isocyanides.

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proposed mechanism

Key Words

amides, TBHP

ID: J54-Y2016