Header

UZH-Logo

Maintenance Infos

Boronic esters of corannulene: potential building blocks toward icosahedral supramolecules


Da Ros, Sara; Linden, Anthony; Baldridge, Kim K; Siegel, Jay S (2015). Boronic esters of corannulene: potential building blocks toward icosahedral supramolecules. Organic Chemistry Frontiers, 2(6):626-633.

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.

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.

Statistics

Citations

Dimensions.ai Metrics
11 citations in Web of Science®
12 citations in Scopus®
9 citations in Microsoft Academic
Google Scholar™

Altmetrics

Downloads

51 downloads since deposited on 12 Nov 2015
6 downloads since 12 months
Detailed statistics

Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2015
Deposited On:12 Nov 2015 07:20
Last Modified:14 Feb 2018 09:39
Publisher:Royal Society of Chemistry
ISSN:2052-4110
OA Status:Hybrid
Publisher DOI:https://doi.org/10.1039/C5QO00009B

Download

Download PDF  'Boronic esters of corannulene: potential building blocks toward icosahedral supramolecules'.
Preview
Content: Published Version
Filetype: PDF
Size: 2MB
View at publisher
Licence: Creative Commons: Attribution 3.0 Unported (CC BY 3.0)