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.

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

Berton G.;Scarso A.
2018

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.
28-giu-2018
Pubblicato
https://pubs.rsc.org/en/content/articlelanding/2018/QO/C8QO00414E#!divAbstract
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11368/2961480
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