Synthesis of Boronate-Based Benzo[fg]tetracene and Benzo[hi]hexacene via Demethylative Direct Borylation.
A demethylative direct borylation is reported, which was applied to the synthesis of benzo[fg]tetracenes containing boronate ester, amide, and thioester substructures. Depending on the heteroatom adjacent to boron, the molecules showed characteristic photophysical properties, molecular arrangements, and chemical stabilities. The key to the successful synthesis is the appropriate choice of the boron source and Brønsted base. The versatility of the direct borylation was demonstrated by the synthesis of a boronate-based benzo[hi]hexacene.
Department of Chemistry, School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda, Hyogo, 669-1337, Japan.
Misa
M
Numano
Department of Chemistry, School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda, Hyogo, 669-1337, Japan.
Naoto
N
Nagami
Department of Chemistry, School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda, Hyogo, 669-1337, Japan.
Soichiro
S
Nakatsuka
Department of Chemistry, School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda, Hyogo, 669-1337, Japan.
Takazumi
T
Katayama
Department of Chemistry, School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda, Hyogo, 669-1337, Japan.
Kiichi
K
Nakajima
Department of Chemistry, School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda, Hyogo, 669-1337, Japan.
Sou
S
Tatsumi
Japan Synchrotron Radiation Research Institute (JASRI), 1-1-1, Kouto, Sayo-cho, Sayo-gun, Hyogo, 679-5198, Japan.
Nobuhiro
N
Yasuda
Department of Chemistry, School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda, Hyogo, 669-1337, Japan. hataka@kwansei.ac.kp.|Elements Strategy Initiative for Catalysts and Batteries, Kyoto University, Katsura, Kyoto, 615-8520, Japan. hataka@kwansei.ac.kp.
Takuji
T
Hatakeyama
aromatic compounds; boronate; borylation; electrophilic substitution