Highly efficient synthesis of C3-symmetric O-alkyl substituted triphenylenes and related Mannich derivatives. Issue 16 (17th July 2018)

• Record Type: Journal Article
• Authors: Berton, Giacomo; Borsato, Giuseppe; Zangrando, Roberta; Gambaro, Andrea; Fabris, Fabrizio; Scarso, Alessandro
• Is Part Of: Organic chemistry frontiers. Volume 5:Issue 16(2018)
• Page Start: 2458
• Page End: 2462
• Publication Date: 2018-07-17
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/c8qo00414e
• Languages: English
• ISSNs: 2052-4110

Abstract

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