Synthesis 2020; 52(22): 3326-3336
DOI: 10.1055/s-0040-1707256
short review

Catalytic C–H Arylation of Tetrathiafulvalenes for the Synthesis of Functional Materials

a  Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo-ku, Kyoto 606-8502, Japan   Email: yori@kuchem.kyoto-u.ac.jp
,
b  Department of Applied Chemistry, Graduate School of Science and Engineering, Ehime University, 3 Bunkyo-cho, Matsuyama, Ehime 790-8577, Japan
c  Research Unit for Power Generation and Storage Materials, Ehime University, Matsuyama, Ehime 790-8577, Japan
,
b  Department of Applied Chemistry, Graduate School of Science and Engineering, Ehime University, 3 Bunkyo-cho, Matsuyama, Ehime 790-8577, Japan
c  Research Unit for Power Generation and Storage Materials, Ehime University, Matsuyama, Ehime 790-8577, Japan
d  Research Unit for Development of Organic Superconductors, Ehime University, Matsuyama, Ehime 790-8577, Japan
› Author Affiliations
This work was supported by JSPS KAKENHI Grant Numbers JP19H00895 and JP19H02690 as well as by JST CREST Grant Number JPMJCR19R4. Furthermore, this work was supported by a Grant-in-Aid for Research Promotion (Ehime University) to the Research Unit for Development of Organic Superconductors and to the Research Unit for Power Generation and Storage Materials.


Abstract

Sulfur-containing functional π-conjugated cores play key roles in materials science, mostly due to their unique electrochemical and photophysical properties. Among these, the excellent electron donor tetrathiafulvalene (TTF) has occupied a central position since the emergence of organic electronics. Peripheral C–H modification of this highly useful sulfur-containing motif has resulted in the efficient creation of new molecules that expand the applications of TTFs. This Short Review begins with the development of the palladium-catalyzed direct C–H arylation of TTF. Subsequently, it summarizes the applications of this efficient C–H transformation for the straightforward synthesis of useful TTF derivatives that are employed in a variety of research fields, demonstrating that the development of a new reaction can have a significant impact on chemical science.

1 Introduction

2 Development of the Palladium-Catalyzed Direct C–H Arylation of TTF

3 Synthesis of TTF-Based Tetrabenzoic Acid and Tetrapyridine for MOFs

4 Synthesis of TTF-Based Tetrabenzaldehyde and Tetraaniline for COFs

5 Tetraarylation of TTFAQ

6 Synthesis of Multistage-Redox TTF Derivatives

7 Miscellaneous Examples

8 Conclusions



Publication History

Received: 19 June 2020

Accepted after revision: 16 July 2020

Publication Date:
08 September 2020 (online)

© 2020. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
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