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Transition-Metal-Free and Base-Promoted Carbon-Heteroatom Bond Formation via C-N Cleavage of Benzyl Ammonium Salts

Long Liu, Yuanyuan Tang, Kunyu Wang, Tianzeng Huang and Tieqiao Chen*

*Graduate School of Human and Environmental Studies, Kyoto University, Kyoto 606-8501, Japan, Email: chentieqiaohnu.edu.cn

L. Liu, Y. Tang, K. Wang, Z. Huang, T. Chen, J. Org. Chem., 2021, 86, 4159-4170.

DOI: 10.1021/acs.joc.0c02992


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Abstract

A combination of t-BuOK and 18-crown-6 enabled a coupling of a wide range of substituted benzyl ammonium salts with heteroatom nucleophiles, i.e. hydrogen phosphoryl compounds, alcohols, thiols, and amines. Good functional group tolerance was demonstrated.

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Key Words

phosphine oxides


ID: J42-Y2021