ChemCatChem誌に掲載決定！

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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 e202401427. (DOI: 10.1002/cctc.202401427)

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

JOC誌に掲載決定！

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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)

TL誌に掲載決定！

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Total synthesis and structural confirmation of (±)-spirocollequins A and B
Keita Ichikawa, Toshiyasu Inuzuka, Hidemi Yoda and Tetsuya Sengoku
Tetrahedron Letters 2022, 107, 154109. (DOI: 10.1016/j.tetlet.2022.154109)

The first total synthesis of antiplasmodial isoindolinone alkaloids, spirocollequins A and B, has been accomplished. The proposed structures of spirocollequins have been supported through the comparison of spectroscopic properties of the synthetic samples with those of natural products as well as single-crystal X-ray diffraction analysis using a synthetic precursor of spirocollequin B.

Journal Information: Impact factor 1.8 (Q3, JCR 2022)

小川君、岩間君の論文がChem.Commun.誌に掲載決定！

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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)

牧野君、飯島さんの論文がBeilsteinJOC誌に掲載決定！

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Bifurcated synthesis of methylene-lactone- and methylene-lactam-fused spirolactams via electrophilic amide allylation of γ-phenylthio-functionalized γ-lactams
Tetsuya Sengoku, Koki Makino, Ayumi Iijima, Toshiyasu Inuzuka and Hidemi Yoda
Beilstein Journal of Organic Chemistry,  2020, 16, 2769–2775. (DOI: 10.3762/bjoc.16.227) 

New synthetic methods for spirolactams bearing an α-methylene-γ-butyrolactone or its analogous methylene-lactam have been developed.

Journal Information: Impact factor 2.883 (Q2, JCR 2020)

白井さん、高野さんの論文がJOC誌に掲載決定！

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Divergent synthesis of methylene lactone- and methylene lactam-based spiro compounds; Utility of amido-functionalized γ-hydroxylactam as a precursor for cytotoxic N,O– and N,N-spiro compounds
Tetsuya Sengoku, Anna Shirai, Ayaka Takano, Toshiyasu Inuzuka, Masami Sakamoto, Masaki Takahashi and Hidemi Yoda
The Journal of Organic Chemistry,  2019, 84, 12532-12541. (DOI: 10.1021/acs.joc.9b02038)

Pharmaceutically attractive methylene lactone- and methylene lactam-based spiro compounds have been synthesized by employing amido-functionalized γ-hydroxylactam as a common intermediate.

Journal Information: Impact factor 4.335 (Q1, JCR 2019)

永井君の論文がSynlett誌に掲載決定！

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New synthetic methodology toward azaspiro-γ-lactones via oxidative C-H spirocyclization reaction
Tetsuya Sengoku, Yuichiro Nagai, Toshiyasu Inuzuka and Hidemi Yoda
Synlett, 2019, 30, 199-202. (DOI: 10.1055/s-0037-1611941)

The key C–H spirolactonization was accomplished by employing iodobenzene diacetate and potassium bromide to afford a variety of azaspiro-γ-lactones in high yields. 

Journal Information: Impact factor 2.369 (Q2, JCR 2017)

浅羽君、Luaさんの論文がJOC誌に掲載決定！

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Controllable monobromination of perylene ring system: synthesis of bay-functionalized perylene dyes
Masaki Takahashi, Kyohei Asaba, Trinh Thi Lua, Toshiyasu Inuzuka, Naohiro Uemura, Masami Sakamoto, Tetsuya Sengoku and Hidemi Yoda
The Journal of Organic Chemistry, 2018, 83, 624-631. (DOI: 10.1021/acs.joc.7b02540)

Practical synthesis of bay-monofunctionalized perylene dyes has been developed based on controllable NBS bromination of tetrabenzyl perylene-3,4,9,10-tetracarboxylate. The ability to perform the convenient and high-yielding synthesis highlights the potential utility of our multifunctional approach to access diverse range of new perylene systems.

Journal Information: Impact factor 4.849 (Q1, JCR 2016)

杉山君、神谷君、前川君の論文がEJOC誌に掲載決定！

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Use of β-Amido Allylboronate as a Nucleophilic Reagent in Catalytic Enantioselective Addition to Isatins
Tetsuya Sengoku, Akihiro Sugiyama, Yuta Kamiya, Ryunosuke Maegawa, Masaki Takahashi and Hidemi Yoda
European Journal of Organic Chemistry, 2017, 1285-1288. (DOI: 10.1002/ejoc.201601612)

A new catalytic system that enables the enantioselective tin-free “amide allylation” of isatins is developed with the aid of a newly prepared (β-amidoallyl)boronate.

Journal Information: Impact factor 3.068 (Q2, JCR 2015)