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Methyl-triflate-mediated dearylmethylation of N-(arylmethyl)carboxamides via the retro-Mannich reaction induced by electrophilic dearomatization/rearomatization in an aqueous medium at room temperature

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Abstract

We have developed a protocol for the dearylmethylation of N-(arylmethyl)carboxamides under metal-free conditions in an aqueous medium at room temperature. This protocol involves methyl triflate-mediated successive C–C and C–N bond cleavages (retro-Mannich reaction) induced by electrophilic dearomatization/rearomatization. The dearomatization/rearomatization strategy can be expected to inspire the development of novel transformations based on the C–C bond cleavage in an environmentally benign manner.

Graphical abstract: Methyl-triflate-mediated dearylmethylation of N-(arylmethyl)carboxamides via the retro-Mannich reaction induced by electrophilic dearomatization/rearomatization in an aqueous medium at room temperature

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Publication details

The article was received on 16 Jan 2019, accepted on 13 Mar 2019 and first published on 29 Mar 2019


Article type: Communication
DOI: 10.1039/C9GC00176J
Citation: Green Chem., 2019, Advance Article

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    Methyl-triflate-mediated dearylmethylation of N-(arylmethyl)carboxamides via the retro-Mannich reaction induced by electrophilic dearomatization/rearomatization in an aqueous medium at room temperature

    H. Peng, J. Ma, W. Luo, G. Zhang and B. Yin, Green Chem., 2019, Advance Article , DOI: 10.1039/C9GC00176J

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