7th International Conference on Green and Sustainable Chemistry and 4th JACI/GSC Symposium, Poster Award(2015年8月)
日本化学会 第95春季年会 優秀講演賞(学術) (2015年5月)
有機合成化学協会研究企画賞(2012年12月)
学内表彰
薬学部若手教員学部長表彰(2021 年 5 月)
2025年
論文
N. Miyamoto, K. Kikushima, H. Sasa, T. Katagiri, N. Takenaga, Y. Kita, T. Dohi, Transition-metal-free dibenzoxazepinone synthesis by hypervalent iodine-mediated chemoselective arylocyclizations of N-functionalized salicylamides. Chem. Commun., 2025, 61(9), 1882-1885 (Themed collection: Chemistry for a Sustainable World – Celebrating Our Community Tackling Global Challenges).
H. China, Y. Yoto, H. Sasa, K. Kikushima, T. Dohi, Reconstructive synthesis of fluorinated [1,2-a]dihydropyridoindolones by a cyclohexadione cut-to-fuse strategy. Adv. Synth. Catal., 2025, 367(3), e202401037 (Hot Topic: Fluorine Chemistry).
総説
T. Dohi, E. E. Elboray, K. Kikushima, K Morimoto, Y. Kita, Iodoarene activation: Take a leap forward toward green and sustainable transformations. Chem. Rev., 2025, 125, in press.
Aleena raju, Subhiksha J., K. Sakthivel, S. Mishra, R. J. Gana, K. Kikushima, T. Dohi, F. V. Singh, Recent advances in metal-catalysed oxidation reactions. R. Soc. Open Sci., 2025, 12(1), 241215.
E. E. Elboray, T. Bae, K. Kikushima, N. Takenaga, Y. Kita, T. Dohi, Metal-free synthesis of benzisoxazolones utilizing ortho-ester and ortho-cyano-functionalized diaryliodonium salts with protected hydroxylamines. J. Org. Chem., 2024, 89(23), 17518–17527.
K. Kikushima, T. Tsuda, N. Miyamoto, Y. Kita, T. Dohi, Borate-mediated aryl polyfluoroalkoxylation under transition-metal-free conditions. Chem. Commun., 2024, 60(76), 10552-10555.
K. Kikushima, K. Komiyama, N. Umekawa, K. Yamada, Y. Kita, T. Dohi, Silver-catalyzed coupling of unreactive carboxylates: Synthesis of α-fluorinated O-aryl esters. Org. Lett., 2024, 26(25), 5347-5352.
“Metal-free new synthesis of benzisoxazolones with diaryliodonium salts” 共同発表, International Society of Heterocyclic Chemistry, 29th Congress of the International Society of Heterocyclic Chemistry (ISHC 2024), Aveiro. (2024年7月)
“Metal-free coupling of diaryliodonium(Ⅲ) salt with fluoroalkoxy boronate -New synthesis of fluoroalkoxy (hetero)arenes-” 共同発表, International Society of Heterocyclic Chemistry, 29th Congress of the International Society of Heterocyclic Chemistry (ISHC 2024), Aveiro. (2024年7月)
“Metal-free heterocycle synthesis from aryl cyclic diketones by fluorinative cut-to-fuse strategy” 共同発表, International Society of Heterocyclic Chemistry, 29th Congress of the International Society of Heterocyclic Chemistry (ISHC 2024), Aveiro. (2024年7月)
“Metal-free dibenzoxazepinone synthesis through chemoselective aromatic coupling with hypervalent iodine reagent and catalyst” 共同発表, The French catalysis community, 18th ICC - International Congress of Catalysis, Lyon. (2024年7月)
“Silver catalyst with iodonium salt: O-arylation of α-fluorocarboxylic acid” 共同発表, The French catalysis community, 18th ICC - International Congress of Catalysis, Lyon. (2024年7月)
2023年
論文
K. Kikushima, K. Yamada, N. Umekawa, N. Yoshio, Y. Kita, T. Dohi, Decarboxylative arylation with diaryliodonium(III) salts: Alternative approach for catalyst-free difluoroenolate coupling to aryldifluoromethyl ketones. Green Chem., 2023, 25(5), 1790-1796. (Cover Feature, Green Chemistry themed collection on International Symposium on Green Chemistry 2022)
E. E. Elboray, T. Bae, K. Kikushima, Y. Kita, T. Dohi, Transition metal-free O-arylation of N-alkoxybenzamides enabled by aryl(TMP)iodonium salts. Adv. Synth. Catal., 2023, 365(16), 2703-2710. (Special Issue: Iodine in Catalysis and Organic Synthesis).
“Arylation of fluorinated acetic acids with diaryliodonium salts” 2nd Workshop on Radical and Electron Transfer Reactions (RETR-2), Shiga. (2023年6月)
学会発表(国際)
“Introduction of difluromethyl group into (herero)arenes via decarboxylative arylation using iodonium(III) salt” 共同発表, Kinka Chemical Society, The 15th International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-15), Kyoto. (2023年11月)
“Silver-catalyzed direct O-arylation of α-fluorinated carboxylic acid with diaryliodonium(III) salt” 共同発表, Kinka Chemical Society, The 15th International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-15), Kyoto. (2023年11月)
“Synthesis of α-fluorinated aryl esters Using diaryliodonium(III) salts” 共同発表, Conferium, 23rd International Symposium on Fluorine Chemistry, Quebec (Canada). (2023年7月)
“Introduction of fluoroalkyl groups into arenes via transient diaryliodonium(III) salts” 共同発表, Conferium, 23rd International Symposium on Fluorine Chemistry, Quebec (Canada). (2023年7月)
“Metal-free arylation via aryl(trimethoxyphenyl)iodonium carboxylates to access functionalized arenes” 共同発表, Elsevier, 23rd Tetrahedron Symposium, Gothenburg (Sweden). (2023年6月)
“Transition-metal-free phenol O-arylation with TMP-iodonium(III) acetates and its application to dibenzoxazepinone synthesis” 共同発表, Elsevier, 23rd Tetrahedron Symposium, Gothenburg (Sweden). (2023年6月)
“Metal-free chemoselective O-arylation of amides with highly reactive TMP-iodonium(III) acetates” 共同発表, Elsevier, 23rd Tetrahedron Symposium, Gothenburg (Sweden). (2023年6月)
2022年
論文
H. Sasa, K. Mori, K. Kikushima, Y. Kita, T. Dohi, μ-Oxo hypervalent iodine-catalyzed oxidative C-H amination for synthesis of benzolactam derivatives. Chem. Pharm. Bull, 2022, 70(2), 106-110.
K. Kikushima, N. Miyamoto, K. Watanabe, D. Koseki, Y. Kita, T. Dohi, Ligand- and counterion-assisted phenol O-arylation with TMP-iodonium(III) acetates. Org. Lett., 2022, 24(10), 1924-1928. (Cover Feature, EurekAlert! press release, Organic Chemistry Portal)
K. Kikushima, A. Morita, E. E. Elboray, T. Bae, N. Miyamoto, Y. Kita, T. Dohi, Transition-metal-free N-arylation of N-methoxysulfonamides and N,O-protected hydroxylamines with trimethoxyphenyliodonium(III) acetates. Synthesis, 2022, 54(23), 5192-5202. (Feature article)
総説
K. Kikushima, E. E. Elboray, J. O. C. Jiménez-Halla, C. R. Solorio-Alvarado, T. Dohi, Diaryliodonium(III) salts in one-pot double functionalization of C–I(III) and ortho C–H bonds. Org. Biomol. Chem. 2022, 20(16), 3231-3248. (Front Cover Feature)
S. E. Shetgaonkar, R. Mamgain, K. Kikushima, T. Dohi, F. V. Singh, Palladium-catalyzed organic reactions involving hypervalent iodine reagents. Molecules 2022, 27(12), 3900-3960. (Special Issue: Applications of Palladium-Catalyzed in Organic Chemistry)
S. Soni, Rimi, V. Kumar, K. Kikushima, T. Dohi, V. V. Zhdankin, R. Kumar, Hypervalent iodine(V) catalyzed reactions. ARKIVOC 2022, vii, 27-56. (Prof. V. V. Zhdankin Hypervalent Iodine Special Issue)
学会発表(国内)
「Chemospecific arylation of protected hydroxylamines and sulfonamides with aryl(TMP)iodonium salt」、共同発表、日本化学会第102春季年会 (2022年3月)
“Transition-metal-free functionalization of (hetero)arenes via highly reactive TMP-iodonium(III) acetates” 共同発表, ISHC, 28th International Society of Heterocyclic Chemistry Congress, Santa Barbara (USA). (2022年8月)
“Environmentally friendly phenol O-arylation with aryl(TMP)-iodonium(III) acetates” 共同発表, Portuguese Chemical Society (PCS), 8th EuChemS Chemistry Congress (ECC8), Lisbon (Portugal). (2022年8月)
“Efficient arylation of heteroatom nucleophiles using TMP-iodonium(III) salts” 共同発表, CNRS, ISGC 2022, La Rochelle (France). (2022年5月)
“Decarboxylative metal-free synthesis of aryl difluorocarbonyl compounds using TMP iodonium(III) salts” 共同発表, CNRS, ISGC 2022, La Rochelle (France). (2022年5月)
2021年
論文
K. Kikushima, K. Matsuki, Y. Yoneda, T. Menjo, K. Kaneko, T. Hanasaki, T. Dohi, Polyfluoroarene-capped thiophene derivatives via fluoride-catalyzed nucleophilic aromatic substitution. Heterocycles, 2021, 103(2), 878-892. (Prof. Kita's Special Issue)
K. Kikushima, H. Koyama, K. Kodama, T. Dohi, Nucleophilic aromatic substitution of polyfluoroarene to access highly
functionalized 10-phenylphenothiazine derivatives. Molecules, 2021, 26(5), 1365-1378. (Special Issue: 25th Anniversary of Molecules - Recent Advances in Organic Synthesis)
T. Shoji, K. Fukushima, T. Menjo, Y. Yamada, T. Hanasaki, K. Kikushima, N. Takenaga, T. Dohi, Triflimide-promoted nucleophilic C-arylation of halopurines to access N7-substituted purine biaryls. Chem. Pharm. Bull., 2021, 69(9), 886-891.
H. Sasa, K. Mori, K. Kikushima, Y. Kita, T. Dohi, μ-Oxo hypervalent iodine-catalyzed oxidative C-H amination for synthesis of benzolactam derivatives. Chem. Pharm. Bull, 2021, in press.
総説
K. Kikushima, R. Kumar, T. Dohi, Progress in [18F]fluorination by using aryliodonium(III) compounds and application for PET tracer syntheses. Mini Rev. Org. Chem., 2020, 18(2), 173-195. (Special Issue: Hypervalent Iodine in Organic Synthesis) Editor's Choice Article
“Efficient arylation of oxygen nucleophiles through diaryliodonium(III) intermediates” 共同発表, CSJ, Pacifichem 2021, Hawaii (online). (2021年12月)
“Efficient synthesis of diaryl ethers using trimethoxyphenyl (TMP) diaryliodonium(III) acetates” 共同発表, CSJ, Pacifichem 2021, Hawaii (online). (2021年12月)
“Selective arylation using diaryliodonium(III) salts bearing ortho-substituted dummy aryl ligand” 共同発表, CSJ, Pacifichem 2021, Hawaii (online). (2021年12月)
“Aryl phenothiazine derivatives through nucleophilic aromatic substitution toward polyfluoroarenes” 共同発表, CSJ, Pacifichem 2021, Hawaii (online). (2021年12月)
“Anodically generated μ-oxo hypervalent iodine catalyst for oxidative dearomatizing reaction” 共同発表, CSJ, Pacifichem 2021, Hawaii (online). (2021年12月)
“Synthesis of new uracil derivatives through the generation of “uracilyne”” 共同発表, CSJ, Pacifichem 2021, Hawaii (online). (2021年12月)
2020年
論文
H. China, K. Tanihara, H. Sasa, K. Kikushima, T. Dohi, Regiodivergent oxygenations of alkoxyarenes by new hypervalent iodine/Oxone system. Catal. Today 2020, 348, 2-8. (Special Issue for Invited Contributors in 1st International Conference on Applied Catalysis & Chemical Engineering)
H. China, H. Yatabe, N. Kageyama, M. Fujitake, K. Kikushima, T. Dohi, New syntheses of haloketo acid methyl esters and their transformation to halolactones by reductive cyclizations. Russ. Chem. Bull., 2020, 69(9), 1804-1810. (150th Mendeleev Special Issue)
K. Komiyama, S. Kobayashi, T. Shoji, K. Kikushima, T. Dohi, Y. Kita, Practical synthesis of diaryliodonium(III) triflates using ArI(OAc)2/TfOH/CH3CN reaction system. Russ. Chem. Bull., 2020, 69(12), 2328—2332. (150th Mendeleev Special Issue)
K. Kikushima, Y. Etou, R. Kamura, I. Takeda, H. Ito, M. Ohashi, S. Ogoshi, Direct transformation of tetrafluoroethylene to trifluorovinylzinc via sp2 C-F bond activation. Org. Lett., 2020, 22(20), 8167-8172.
総説
H. China, K. Kikushima, R. Kumar, T. Dohi, Halogen-induced controllable cyclizations as diverse heterocycle synthetic strategy. Molecules 2020, 25(24), 6007-6040. (Special Issue: Halogen-Controlled Synthesis of Useful Organic Molecules)
N. Takenaga, T. Shoji, T. Menjo, A. Hirai, S. Ueda, K. Kikushima, T. Hanasaki, T. Dohi, Nucleophilic arylation of halopurines facilitated by Bronsted acid in fluoroalcohol. Molecules 2019, 24(21), 3812-3821. (Modern Strategies for Heterocycle Synthesis)
H. China, D. Koseki, K. Samura, K. Kikushima, Y. In, T. Dohi, Dataset on synthesis and crystallographic structure of phenyl(TMP)iodonium(III) acetate. Data Brief 2019, 25, 104063.
総説
K. Kikushima, H. China, T. Dohi, Asymmetric construction of heterocycles via dearomative coupling and addition reactions of phenol and aniline derivatives. Heterocycles 2019, 98, 1489-1511. (Invited Review)
T. Moriuchi, K. Kikushima, ハロゲン化物塩をハロゲン源とする酸化的ハロゲン化反応 有機合成化学協会誌 2019, 77, 227-235.
“Aryl trifluoroacetoxylation via catalytic ligand transfer of diaryliodonium(III) salts” 共同発表, 26th International symposium: Synthesis in Organic Chemistry, Cambridge. (2019年7月)
“Selective synthesis of cyclic organoiodine(III) without contamination of hazardous pentavalent compound” 共同発表, XXI Mendeleev Congress on General and Applied Chemistry, St. Petersburg. (2019年9月)
“Synthesis of aryl esters through accelerated ligand coupling of diaryliodonium(III) salts” 共同発表, 27th International Society of Heterocyclic Chemistry Congress, Kyoto. (2019年9月)
“Selective p-quinone formation through aryl iodonium(III) intermediate” 共同発表, International Conference "Catalysis and Organic Synthesis" (ICCOS2019), Moscow. (2019年9月)
解説
菊嶌孝太郎,「Transformation of perfluoro compounds」化学工業, 化学工業社, 2019, 78, 600-608.
M. Ohashi, N. Ishida, K. Ando, Y. Hashimoto, A. Shigaki, K. Kikushima, S. Ogoshi, CuI-catalyzed pentafluoroethylation of aryl iodides in the presence of tetrafluoroethylene and cesium fluoride: Determining the route to the key pentafluoroethyl CuI intermediate. Chem.-Eur. J. 2018, 24, 9794-9798.
K. Kikushima, M. Grellier, M. Ohashi, S. Ogoshi, Transition-metal-free catalytic hydrodefluorination of polyfluoroarenes by concerted nucleophilic aromatic substitution with a hydrosilicate. Angew. Chem., Int. Ed. 2017, 56, 16191-16196.
M. Ohashi, T. Adachi, N. Ishida, K. Kikushima, S. Ogoshi, Synthesis and reactivity of fluoroalkyl copper complexes by the oxycupration of tetrafluoroethylene. Angew. Chem., Int. Ed. 2017, 56, 11911-11915.
K. Kikushima, H. Sakaguchi, H. Saijo, M. Ohashi, S. Ogoshi, Copper-mediated one-pot synthesis of trifluorostyrene derivatives from tetrafluoroethylene and arylboronate. Chem. Lett. 2015, 44, 1019-1021.
M. Ohashi, H. Shirataki, K. Kikushima, S. Ogoshi, Nickel-catalyzed formation of fluorine-containing ketones via the selective cross-trimerization reaction of tetrafluoroethylene, ethylene, and aldehydes. J. Am. Chem. Soc. 2015, 137, 6496-6499.
M. Ohashi, T. Kawashima, T. Taniguchi, K. Kikushima, S. Ogoshi, 2,2,3,3-Tetrafluoronickelacyclopentanes generated via the oxidative cyclization of tetrafluoroethylene and simple alkenes: A key intermediate in nickel-catalyzed C-C bond-forming reactions. Organometallics 2015, 34, 1604-1607.
R. Doi, K. Kikushima, M. Ohashi, S. Ogoshi, Synthesis, characterization, and unique catalytic activities of a fluorinated nickel enolate. J. Am. Chem. Soc. 2015, 137, 3276-3282.
K. Kikushima, Y. Nishina, Synthesis of 2-arylphenol derivatives through a one-pot Suzuki-Miyaura coupling/dehydrogenative aromatization sequence with Pd/C catalysis. Eur. J. Org. Chem. 2015, 5864-5868.
J. C. Holder, E. D. Goodman, K. Kikushima, M. Gatti, A. N. Marziale, B. M. Stoltz, Synthesis of diverse β-quaternary ketones via palladium-catalyzed asymmetric conjugate addition of arylboronic acids to cyclic enones. Tetrahedron 2015, 71, 5781-5792.
K. Kikushima, Y. Nishina, Copper-catalyzed oxidative aromatization of 2-cyclohexen-1-ones to phenols in the presence of catalytic hydrogen bromide under molecular oxygen. RSC Adv. 2013, 3, 20150-20156.
Y. Nishina, B. Ohtani, K. Kikushima, Bromination of hydrocarbons with CBr4, initiated by light-emitting diode irradiation. Beilstein J. Org. Chem. 2013, 9, 1663-1667.
J. C. Holder, L. Zou, A. N. Marziale, P. Liu, Y. Lan, M. Gatti, K. Kikushima, K. N. Houk, B. M. Stoltz, Mechanism and enantioselectivity in palladium-catalyzed conjugate addition of arylboronic acids to β substituted cyclic enones: Insights from computation and experiment. J. Am. Chem. Soc. 2013, 135, 14996-15007.
K. Kikushima, J. C. Holder, M. B. Gatti, B. M. Stoltz, Palladium-catalyzed asymmetric conjugate addition of arylboronic acids to five-, six-, and seven-membered β-substituted cyclic enones: enantioselective construction of all-carbon quaternary stereocenters. J. Am. Chem. Soc. 2011, 133, 6902-6905.
K. Kikushima, T. Moriuchi, T. Hirao, Vanadium-catalyzed oxidative bromination promoted by Bronsted acid or Lewis acid. Tetrahedron 2010, 66, 6906-6911.
K. Kikushima, T. Moriuchi, T. Hirao, Oxidative bromination reaction using vanadium catalyst and aluminum halide under molecular oxygen. Tetrahedron Lett. 2010, 51, 340-342.
T. Moriuchi, K. Kikushima, T. Kajikawa, T. Hirao, Vanadium-catalyzed oxidative aromatization of 2-cyclohexenones under molecular oxygen. Tetrahedron Lett. 2009, 50, 7385-7387.
K. Kikushima, T. Moriuchi, T. Hirao, Vanadium-catalyzed oxidative bromination under atmospheric oxygen. Chem.-Asian J. 2009, 4, 1213-1216.
T. Moriuchi, M. Yamaguchi, K. Kikushima, T. Hirao, An efficient vanadium-catalyzed bromination reaction. Tetrahedron Lett. 2007, 48, 2667-2670.
解説
K. Kikushima, Transition metal-mediated or -catalyzed nucleophilic fluorination for aryl fluorides with metal fluoride salts. 有機合成化学協会誌 2015, 73, 80-81.