Showing papers by "Seiji Suga published in 2013"
TL;DR: In this paper, the addition reactions of diaryl disulfides (ArSSAr) to alkenes and alkynes were achieved with a catalytic amount of an arylbis(arylthio)sulfonium ion (ArS(ArssAr)+), which was generated and accumulated by low-temperature electrolysis of ArSSAr, to give the corresponding diarylthiolated products.
22 citations
TL;DR: The first synthesis of hexa(furan-2-yl)benzene derivatives is described and their π-extended derivatives were also synthesized by Suzuki-Miyaura coupling between hexakis(5-Bpinfuran- 2-yl), Bpin = (pinacolato)boryl and several aryl iodides.
Abstract: The first synthesis of hexa(furan-2-yl)benzene derivatives is described. The RhCl3/i-Pr2NEt-catalyzed cyclotrimerization of di(furan-2-yl)acetylenes was an effective method for constructing hexa(furan-2-yl)benzene derivatives in good yields. Their π-extended derivatives were also synthesized by Suzuki–Miyaura coupling between hexakis(5-Bpinfuran-2-yl)benzene (Bpin = (pinacolato)boryl) and several aryl iodides.
20 citations
TL;DR: In this article, the first electro-reductive halogen-deuterium exchange reaction and methylation reaction was reported under metal-free and mild conditions, and the reaction in CD3CN gave deuterated product selectively.
Abstract: Deuterium-labeled compounds are playing key roles in many scientific fields such as pharmaceutical science and mechanistic studies of organic reactions.13 One of the most facile and straightforward methods to introduce a deuterium atom selectively is reductive halogen-deuterium exchange reactions. Several conditions, such as using a radical mediator (e.g. tin hydride47 and samarium diiodide8) or light irradiation,9 have been reported. Meanwhile, we have studied electro-organic transformations,1013 and recently reported electro-reductive intramolecular cyclization of haloarenes bearing an alkene moiety in acetonitrile.14 During the course of the mechanistic study on the reactions, we found that the cyclized radical intermediate would be protonated by acetonitrile, and the reaction in CD3CN gave deuterated product selectively. These results prompted us to study an electro-reductive halogen-deuterium exchange reaction under metal-free and mild conditions. Screening of the reaction conditions revealed that 9-fluorenone was an efficient mediator for the reaction, and we unexpectedly found that dehalomethylation also proceeded under similar conditions. We herein report the first electro-reductive halogen-deuterium exchange reaction and methylation reaction.
16 citations
13 citations
TL;DR: In this article, a diaryl disulfide addition to carbon-carbon multiple bonds was achieved with a catalytic amount of an electrogenerated acid (EGA), which was produced by the electrolysis of Bu4N+B(C6F5)4−/CH2Cl2.
Abstract: Addition of diaryl disulfides to carbon–carbon multiple bonds was achieved with a catalytic amount of an electrogenerated acid (EGA), which was produced by the electrolysis of Bu4N+B(C6F5)4−/CH2Cl2...
8 citations
TL;DR: In this article, an electro-oxidative Wacker-type reaction was developed in PEG/CH3CN thermomorphic biphasic system, and the heterogeneous solution was turned into homogeneous solution with heating to 60°C.
Abstract: Electro-oxidative Wacker-type reaction has been developed in PEG/CH3CN thermomorphic biphasic system. The heterogeneous solution was turned into homogeneous solution with heating to 60°C, and electro-oxidative Wackertype reactions of alkenes bearing long alkyl chains proceeded smoothly to afford methyl ketones in good yields. The recycling of PEG phase containing Pd has also been achieved. © The Electrochemical Society of Japan, All rights reserved.
5 citations