Department of Applied Chemistry, Graduate School of Engineering Osaka University MINAKATA Lab. Synthetic Organic Chemistry Research Group

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論文 Publication List at MINAKATA Lab.

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"Transition-metal-free Benzylic C–H Bond Intermolecular Amination Utilizing Chloramine-T and I2"
Youhei Takeda, Junpei Hayakawa, Kazuki Yano, and Satoshi Minakata*
Chem. Lett. 2012, 41, 1672–1674. DOI: 10.12461/cl.2012.1672

Abstract: An intermolecular benzylic C­H bond amination utilizing the combination of chloramine-T and I2 without the aid of transition-metal catalysts has been developed. The reaction was found applicable to a variety of benzene-substituted alkanes, as well as to an adamantane derivative to give N-alkylated ptosylamides in good yields.

"Nucleophilic Ring-Opening of N-o-Nosylaziridines with N-Chloro-N-Sodiocarbamate: Facile Preparation of Differentially Protected Vicinal Diamines"
Youhei Takeda, Yuta Murakami, Yuki Ikeda, and Satoshi Minakata*
Asian J. Org. Chem. 2012, 1, 226–230. DOI: 10.1021/ajoc.201200070


Abstract: A mild nucleophilic ring-opening reaction of activated aziridines with N-chloro-N-sodio-tert-butylcarbamate, which gives differentially protected vicinal diamine derivatives, has been developed. The two protecting groups are selectively removable, and the total synthesis of a long-chain fatty acids oxidation inhibitor, emeriamine, was achieved by using the present method.

"Cyclizative Atmospheric CO2 Fixation by Unsaturated Amines with t-BuOI Leading to Cyclic Carbamates"
Youhei Takeda, Sota Okumura, Saori Tone, Itsuro Sasaki, and Satoshi Minakata*
Org. Lett. 2012, 14, 4874–4877. DOI: 10.1021/ol302201q

* Highlighted in "Noteworthy Chemistry" (ACS, October 1, 2012)! see the detail

Abstract: A cyclizative atmospheric CO2 fixation by unsaturated amines such as allyl and propargyl amines under mild reaction conditions, efficiently leading to cyclic carbamates bearing a iodomethyl group, have been developed utilizing tert-butyl hypoiodite (t-BuOI).

"Selective Functionalization of Fullerenes with N,N-Dihalosulfonamides as an N1 Unit: Versatile Syntheses of Aza[60]fulleroids and Aziridino[60]fullerenes and their Application to Photovoltaic Cells"
Toshiki Nagamachi, Youhei Takeda, Kazuhisa Nakayama, and Satoshi Minakata*
Chem. Eur. J. 2012, 18, 12035-12045. DOI: 10.1002/chem.201201680

Abstract: Highly selective and versatile methods for the synthesis of aza[60]fulleroids and aziridino[60]fullerenes from C60 have been developed. The reactions utilized N,N-dihalosulfonamides as an N1 source. The photophysical, electrochemical, and thermal properties of the iminofullerenes were investigated by means of UV/Vis spectroscopy, cyclic voltammetry, and thermogravimetry, respectively. Furthermore, photovoltaic cells based on the synthesized iminofullerenes were fabricated. The power conversion efficiencies (PCEs) of the devices showed moderate values ranging from 1.33 to 2.35 %.

"Oxidative Dimerization of Aromatic Amines Using tBuOI under Mild Conditions: Entry to Unsymmetric Aromatic Azo Compounds"
Youhei Takeda, Sota Okumura, and Satoshi Minakata*
Angew. Chem., Int. Ed. 2012, 51, 7804-7808. DOI: 10.1002/anie.201202786

* Selected as a "Hot Paper"! see the detail
* Highlighted in "ワイリー・サイエンスカフェ"! link
* Highlighted in "Noteworthy Chemistry" ACS, August 27, 2012! see the detail
* Highlighted in Synfacts (2012, 8, 1091)! see the detail

Abstract:An oxidative dimerization reaction of aromatic amines utilizing tert-butyl hypoiodite (tBuOI) under mild reaction conditions leads to aromatic azo compounds. The method allows access to unsymmetric aromatic azo compounds, which are difficult to prepare by conventional synthetic methods, in a selective manner.

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