Synthesis and properties of tetrathiafulvalenes bearing 6-aryl-1,4-dithiafulvenes.

Authors :: Yoshimura A
Kimura H
Kagawa K
Yoshioka M
Itou T
Vasu D
Shirahata T
Yorimitsu H
Misaki Y
Source :: Beilstein journal of organic chemistry [Beilstein J Org Chem] 2020 May 12; Vol. 16, pp. 974-981. Date of Electronic Publication: 2020 May 12 (Print Publication: 2020).
Publication Year :: 2020
Abstract: Novel multistage redox tetrathiafulvalenes (TTFs) bearing 6-aryl-1,4-dithiafulvene moieties were synthesized by palladium-catalyzed direct C-H arylation. In the presence of a catalytic amount of Pd(OAc) <subscript>2</subscript> , P( t -Bu <subscript>3</subscript> )·HBF <subscript>4</subscript> , and an excess of Cs <subscript>2</subscript> CO <subscript>3</subscript> , the C-H arylation of TTF with several aryl bromides bearing 1,3-dithiol-2-ylidenes took place efficiently to produce the corresponding π-conjugated molecules. We also succeeded in the estimation of the oxidation potentials and number of electrons involved in each oxidation step of the obtained compounds by digital simulations.<br /> (Copyright © 2020, Yoshimura et al.; licensee Beilstein-Institut.)

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