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


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)2, P(t-Bu3)·HBF4, and an excess of Cs2CO3, the C-H arylation of TTF with several aryl bromides bearing 1,3-dithiol-2-ylidenes took place efficiently to produce the corresponding ?-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.

SUBMITTER: Yoshimura A 

PROVIDER: S-EPMC7237811 | biostudies-literature | 2020

REPOSITORIES: biostudies-literature

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

Yoshimura Aya A   Kimura Hitoshi H   Kagawa Kohei K   Yoshioka Mayuka M   Itou Toshiki T   Vasu Dhananjayan D   Shirahata Takashi T   Yorimitsu Hideki H   Misaki Yohji Y  

Beilstein journal of organic chemistry 20200512


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)<sub>2</sub>, P(<i>t</i>-Bu<sub>3</sub>)·HBF<sub>4</sub>, and an excess of Cs<sub>2</sub>CO<sub>3</sub>, 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 estimatio  ...[more]

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