Conference and Journal Presentations
2022
Journal
| Aerobic photooxidation of toluene derivatives into carboxylic acids with bromine-water under catalyst-free conditions開く |
| Aerobic photooxidation of toluene derivatives into carboxylic acids with bromine-water under catalyst-free conditions. Kirihara, M.; Sakamoto, Y.; Yamahara, S.; Kitajima, A.; Kugisaki, N.; Kimura, Y. Synlett, 2022, 33, 1670-1674.A novel method was developed to synthesize the corresponding benzoic acid derivatives in high yields by adding 2 equivalents of bromine to toluene derivatives and irradiating them with visible or ultraviolet light in the presence of air. |
| Synthesis of sulfonyl halides from disulfides or thiols using sodium hypochlorite pentahydrate (NaOCl·5H2O) crystals開く |
| Synthesis of sulfonyl halides from disulfides or thiols using sodium hypochlorite pentahydrate (NaOCl·5H2O) crystals Kirihara, M.; Yamahara, S.; Okada, T.; Matsumuro, H.; Kinoshita, Y.; Titajima, A.;Takamura, Y.; Odagiri, T.; Asawa, T. Sugiyama, Y.; Kimura, Y. Synthesis 2022, 54, 4120-4128. Sulfonyl chlorides were synthesized by the reaction of disulfides or thiols with sodium hypochlorite pentahydrate in acetic acid, and sulfonyl bromides were obtained in the presence of NaBr. A simple synthetic method was developed to obtain sulfonyl chlorides by blowing carbon dioxide gas through benzotrifluoride solvent instead of acetic acid. |
Conference Presentations
| Sulfonyl fluoride using potassium fluoride with sodium hypochlorite pentahydrate開く |
| Watanabe, M.; Yamahara, S.; Okada, T.; Kimura, Y.; Takizawa, S.; Kirihara. M. 45th Fluorine Conference of Japan, P-19, Kyoto, November 1, 2022. |
| Aerobic photo oxidation of toluenes to benzoic acids by HBr-NaOCl •5H2O開く |
| Kitajima, A.; Tanaka, T.; Takamura, Y.; Kugisaki, N.; Kimura, Y.; Kirihara, M. The Japanese Society for Process Chemistry, 2022 Summer Symposium, 1P-21；Toyama, June 30, 2022. |
| Catalysts free aerobic photo-oxidation of aromatic aldehydes to benzoic acids開く |
| Takamura, Y.; Kitajima, A.;Yamahara, S.; Kugisaki, N.; Kimura, Y.; Kirihara, M. The Japanese Society for Process Chemistry 2022 Summer Symposium 1P-22；Toyama, June 30, 2022. |
| Practical synthesis of sulfonyl fluoride using potassium fluoride開く |
| Yamahara, S.; Watanabe, M; Kimura, Y.; Kirihara, M. The Japanese Society for Process Chemistry 2022 Summer Symposium 1P-23；Toyama, June 30, 2022. |
| Itaconyl dichloride for the synthesis of polyesters/polyamides開く |
| Aoki, Y.; Kawatani, R.; Kousaka, Y.; Matsuura, D.; Onogawa, Y,; Kimura, Y. 31th Polymer Materials Forum, 2PA17, Tokyo, November 15, 2022, |
2021
Journal
| Chloroamidation of alkenes using sodium hypochlorite pentahydrate and its application to synthesis of aziridines開く |
| Chloroamidation of alkenes using sodium hypochlorite pentahydrate and its application to synthesis of aziridines Kirihara, M.; Adachu, K.; Sakamoto, Y.; Tujimoto, K.; Yamahara, S.; Matsushima, R.; Namba, Y.; Sato, K.; Kamada, T.; Kimura, Y.; Takizawa, S. Heterocycles 2021, 103, 699-706. The reaction of sodium hypochlorite pentahydrate and nitrile compounds with alkenes in the absence of a catalyst gave chloroamidation products, and a novel route was developed to synthesize aziridine derivatives by treatment with alkali. |
| Synthesis of polyarylate and aliphatic polyesters by divalent acyl-1,2,4-triazole: A route to metal-free synthesis at low temperature開く |
| Synthesis of polyarylate and aliphatic polyesters by divalent acyl-1,2,4-triazole: a route to metal-free synthesis at low temperature Kohsaka, Y.; Mori, I.; Homma, K.; Akae, Y.; Matuura, D.; Kimura, Y. Polymer J. 2021, 53, 887-893. A new method was developed to synthesize various polyesters from bifunctional acyltriazoles and alcohols under halogen-free conditions without using metal catalysts. |
| Oxidation of fluoroalkyl alcohols using sodium hypochorite pentahydrate開く |
| Oxidation of fluoroalkyl alcohols using sodium hypochorite pentahydrate Kirihara, M.; Suzuki, K.; Nakakura, K.; Saito, K.; Nakamura, R.; Tujimoto, K.; Sakamoto, Y.; Kikkawa, Y.; Shimazu, H.; Kimura, Y. J. Fluorine Chem. 2021, 243, 109719 It is known that alcohols with fluoro chains such as CF3 and CHF2 are not easily oxidized. Oxidation of fluorochain-containing secondary alcohols to the ketones and primary alcohols to the aldehydes with sodium hypochlorite pentahydrate in the presence of TEMPO were found to occur in high yields. |
2020
Journal
| Organic syntheses using sodium hypochlorite pentahydrate (NaOCl • 5H2O) crystals開く |
| Kirihara, M.; Okada, T.; Asawa, T.; Sugiyama, Y.; Kimura,Y. Journal of Synthetic Oraganic Chemistry, Japan, Vol. 78, pp 11–27, 2020. 2017 Synthetic Organic Chemistry Award, Japan |
2019
Journal
| Sodium hypochlorite pentahydrate as a reagent for the cleavage of trans-cyclic glycols 開く |
| Sodium hypochlorite pentahydrate as a reagent for the cleavage of trans-cyclic Glycols trans-cyclic Kirihara, M.; Osugi, R.; Saito, K.; Adachi, K.; Yamazaki, K.; Matsushima, R.; Kimura, Y. J. Org. Chem. 2019, 84, 8330-8336. Trans-1,2-glycols, which are not easily oxidized, were efficiently cleaved by sodium hypochlorite pentahydrate to give dicarbonyl compounds. |
| Direct Formylation of fluorine-containing aromatics with dichloromethyl alkyl ethers開く |
| Direct Formylation of florine-containing aromatics with dichloromethyl alkyl ethers Warashina, T.; Matsuura, D.; Kimura, Y. Chem. Pharm. Bull. 2019, 67, 587-593. Highlighted paper selected by editor-in-chief Formylations of fluorine-containing aromatic compounds with dichloromethyl alkyl ethers were investigated. Dichloromethyl propyl ether and dichloromethyl butyl ether applied to the formylation of fluorine-containing aromatics to give the corresponding aldehydes in good yields. |
| Regioselective formylation of pyrrole-2-carboxylate: Crystalline Vilsmeier reagent vs dichloromethyl alkyl ether開く |
| Regioselective formylation of pyrrole-2-carboxylate: crysatalline Vilsmeier reagent vs dichloromethyl alkyl ether Warashina, T.; Matsuura, D.; Sengoku, T.; Takahashi, M.; Yoda, H; Kimura, Y. Org. Process Res. Dev. 2019, 23, 614-618. A novel synthetic method for solid Vilsmeier reagents and dichloromethyl alkyl ethers was developed. Formylation of pyrroles with an ester group at the 2-position were investigated with the reagents above, and were found to be formylated with high selectivity at different positions. Those products are useful medicinal raw materials. |
| A novel synthetic method for solid Vilsmeier reagents and dichloromethyl alkyl ethers was developed. Formylation of pyrroles with an ester group at the 2-position were investigated with the reagents above, and were found to be formylated with high selectivity at different positions. Those products are useful medicinal raw materials.開く |
| A concise, catalyst-free synthesis of Davis’ oxaziridines using sodium hypochlorite Kitagawa, S.; Mori, H.; Odagiri, T.; Suzuki, K.; Kikkawa, Y.: Osugi.; R.; Takizawa, S.; Kimura, Y.; Kirihara, M. SynOpen 2019, 3, 21-25. A highly selective synthesis of N-sulfonyloxaziridine (Davis' oxaziridine) was developed by reaction of N-sulfonylimine with sodium hypochlorite pentahydrate without any catalyst which is a less dangerous oxidation method. |
| Efficient preparation of dichloromethyl alkyl ethers and their application in the formylation of aromatic compounds: Scope and limitations開く |
| Efficient preparation of dichloromethyl alkyl ethers and their application in the formylation of aromatic compounds: scope and limitations Warashina, T.; Matsuura, D.; Kimura, Y. Tetrahedron 2019, 75, 608-616. A new synthetic method for dichloromethyl alkyl ethers using alkyl formate and oxalyl chloride in the presence of N-methylformanilide was developed, and their formylating abilities were examined. There was a correlation between the length of the alkyl group and the reaction substrate. |