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Highly efficient synthesis of C3-symmetric O-alkyl substituted triphenylenes and related Mannich derivatives

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Abstract

C 3 -Symmetric tris-benzyl-O-substituted hexahydroxytriphenylene (HHTP) was prepared through selective ring opening with DIBAL-H in 48% yield (38% from HHTP in a two-step synthesis) avoiding the use of noxious, expensive and limited market availability reagents, with complete recovery of the undesired Cs co-product that is quantitatively recovered and converted back into HHTP. The C3-symmetric triphenylene product was further functionalized through substitution, deprotection and Mannich condensation reactions affording a series of C3-symmetric functionalized scaffolds in good yields for supramolecular applications.

Graphical abstract: Highly efficient synthesis of C3-symmetric O-alkyl substituted triphenylenes and related Mannich derivatives

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Publication details

The article was received on 23 Apr 2018, accepted on 28 Jun 2018 and first published on 28 Jun 2018


Article type: Research Article
DOI: 10.1039/C8QO00414E
Citation: Org. Chem. Front., 2018, Advance Article
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    Highly efficient synthesis of C3-symmetric O-alkyl substituted triphenylenes and related Mannich derivatives

    G. Berton, G. Borsato, R. Zangrando, A. Gambaro, F. Fabris and A. Scarso, Org. Chem. Front., 2018, Advance Article , DOI: 10.1039/C8QO00414E

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