C3-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 with limited market availability reagents, with complete recovery of the undesired Cs co-product that is quantitatively recovered and converted back to 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
Autori: | A. Scarso (Corresponding) |
Data di pubblicazione: | 2018 |
Titolo: | Highly Efficient Synthesis of C3-symmetry O-alkyl Substituted Triphenylene and Related Mannich Derivatives |
Rivista: | ORGANIC CHEMISTRY FRONTIERS |
Digital Object Identifier (DOI): | http://dx.doi.org/10.1039/C8QO00414E |
Volume: | 5 |
Appare nelle tipologie: | 2.1 Articolo su rivista |
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