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Synthetic Organic Chemistry Laboratory
Visible-Light-Induced Desulfurative Coupling of Alkyl Benzothiazolyl Sulfides with Electron-Deficient Alkenes/Alkynes: Dual Role of Base-Activated Hantzsch Ester
Tetsuya Sengoku, Koki Matsune, Takuma Shimotori, Nagisa Kikuchi, Haruto Hijikata, Shun Nishioka, and Reo Takahashi
ChemCatChem, 2025, 17, e202401427. (DOI: 10.1002/cctc.202401427) Open Access
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The Hantzsch ester anion acts not only as a photoreductant in the catalyst-free desulfurative coupling of alkyl benzothiazolyl sulfides with alkenes/alkynes, but also as a sacrificial reductant in an alternative organocatalytic reaction. The utility of this protocol is expanded to radical C-glycosylation, which includes a protective group-free substrate.
ChemRxiv, DOI:10.26434/chemrxiv-2024-bqs8z
Efficient Visible-Light-Induced π-Extension of Perylene Tetraesters: An Investigation on Regioselectivity
Keisuke Fujimoto, Shingo Miyano, Kenshin Norizuki, Toshiyasu Inuzuka, Tetsuya Sengoku, and Masaki Takahashi
European Journal of Organic Chemistry, 2024, 27, e202400734. (DOI: 10.1002/ejoc.202400734)
This study reports a visible-light-induced π-extension of perylene tetraesters using blue LED irradiation. The synthesis revealed how substituent effects on aromatic groups influence regioselectivity. Theoretical analysis highlighted bond alteration in aromatic rings as a key factor.
Visible-light-induced reductive coupling of arylacetylenes with benzothiazole sulfones
Tetsuya Sengoku, Haruka Iwama, Takuma Shimotori, Keisuke Fujimoto, Toshiyasu Inuzuka, Koki Matsune, Hidemi Yoda
The Journal of Organic Chemistry 2023, 88, 12776-12782. (DOI: 10.1021/acs.joc.3c01554)
The reductive coupling of alkyl or benzylic benzothiazole sulfones with arylacetylenes are performed in the presence of Hantzsch esters and K2CO3 under visible-light irradiation. The utility of this protocol is expanded to α-deuterative coupling using a deuterated Hantzsch ester, furnishing the corresponding alkenes with high deuterium incorporation.
Journal Information: Impact factor 3.6 (Q1, JCR 2023)
A heavy-metal-free desulfonylative Giese-type reaction of benzothiazole sulfones under visible-light conditions
Tetsuya Sengoku, Daichi Ogawa, Haruka Iwama, Toshiyasu Inuzuka and Hidemi Yoda
Chemical Communications, 2021, 57, 9858–9861. (DOI: 10.1039/D1CC03833H)
A heavy-metal-free desulfonylative Giese-type reaction has been achieved by using Hantzsch ester as a photoreductant under blue light.
Journal Information: Impact factor 6.065 (Q1, JCR 2021)