Issue 6, 2015

Boronic esters of corannulene: potential building blocks toward icosahedral supramolecules

Abstract

Direct iridium-catalyzed multi-borylation provides a valuable tool for the symmetric functionalization of various polycyclic aromatic hydrocarbons, inter alia, regular fivefold derivatization of corannulene. In this paper, highly efficient microwave-assisted synthesis of 1,3,5,7,9-(Bpin)5-corannulene is reported, resulting in a significant decrease in reaction time compared to the routine bench-top preparation. In addition, conversion to more reactive boron species, such as the corresponding pentatrifluoroborate and pentaboronic acid, was realized under mild conditions in excellent yields. 1,3,5,7,9-corannulene pentaboronic acid gave further access to a series of boronic esters of corannulene via simple alcohol exchange. This convenient methodology to 1,3,5,7,9-corannulene pentaboronic acid portends its ability to serve as a key building block for formation of icosahedral supramolecules, alone or together with suitable bridging ligands.

Graphical abstract: Boronic esters of corannulene: potential building blocks toward icosahedral supramolecules

Associated articles

Supplementary files

Article information

Article type
Research Article
Submitted
05 Jan 2015
Accepted
12 Mar 2015
First published
24 Mar 2015
This article is Open Access
Creative Commons BY license

Org. Chem. Front., 2015,2, 626-633

Author version available

Boronic esters of corannulene: potential building blocks toward icosahedral supramolecules

S. Da Ros, A. Linden, K. K. Baldridge and J. S. Siegel, Org. Chem. Front., 2015, 2, 626 DOI: 10.1039/C5QO00009B

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