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

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 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.



Titolo: Highly efficient synthesis of C3-symmetric O-alkyl substituted triphenylenes and related Mannich derivatives
Autori: 
BERTON, GIACOMO
SCARSO, ALESSANDRO (Corresponding)
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Data di pubblicazione: 2018
Data ahead of print: 28-giu-2018
Stato di pubblicazione: Pubblicato
Rivista: 
ORGANIC CHEMISTRY FRONTIERS  
Abstract: 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 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.
Handle: http://hdl.handle.net/11368/2961480
Digital Object Identifier (DOI): http://dx.doi.org/10.1039/c8qo00414e
URL: https://pubs.rsc.org/en/content/articlelanding/2018/QO/C8QO00414E#!divAbstract
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