Synthesis 2018; 50(15): 2867-2877
DOI: 10.1055/s-0037-1610165
short review
© Georg Thieme Verlag Stuttgart · New York

Synthetic Strategies for the Regioselective Functionalization of Tribenzotriquinacenes

a   Universität Würzburg, Institut für Organische Chemie, Am Hubland, 97074 Würzburg, Germany   eMail: florian.beuerle@uni-wuerzburg.de
b   Universität Würzburg, Center for Nanosystems Chemistry (CNC), & Bavarian Polymer Institute (BPI), Theodor-Boveri-Weg, 97074 Würzburg, Germany
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a   Universität Würzburg, Institut für Organische Chemie, Am Hubland, 97074 Würzburg, Germany   eMail: florian.beuerle@uni-wuerzburg.de
b   Universität Würzburg, Center for Nanosystems Chemistry (CNC), & Bavarian Polymer Institute (BPI), Theodor-Boveri-Weg, 97074 Würzburg, Germany
› Institutsangaben
The authors thank the Fonds der Chemischen Industrie (Liebig fellowship for F.B.), the DFG (BE4808/2-1) and the Bavarian Ministry for Science, Research and the Arts (Collaborative Research Network ‘Solar Technologies Go Hybrid’ and Bavarian Polymer Institute) for their generous financial support.
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Publikationsverlauf

Received: 24. April 2018

Accepted: 27. April 2018

Publikationsdatum:
18. Juni 2018 (online)


Abstract

The rigid molecular scaffold of the tribenzotriquinacenes (TBTQs) has emerged as a versatile structural platform that possesses unique geometrical features and allows for an orthogonal arrangement of organic functional substituents or convex-concave interactions. In this review, we summarize and discuss important synthetic strategies for a regioselective functionalization at the four distinct positions of the TBTQ basic framework, namely, apical, bridgehead, ortho, and outer rim.

1 Introduction

2 Structure and Synthesis of TBTQs

3 Bridgehead Functionalization

4 Outer Rim Functionalization

5 ortho-Functionalization

6 Apical Functionalization

7 Conclusion and Outlook