Organic Chemistry Laboratory, Nagoya University

 

Kei Murakami

Institute of Transformative Bio-Molecules, Nagoya University
Furo-cho, Chikusa-ku, Nagoya 464-8602, Japan

E-mail: murakami[at]chem.nagoya-u.ac.jp
Phone: +81-52-789-4525, Fax: +81-52-788-6098

【Education and academic experience】

2007 B.S. in Department of Engineering Kyoto University (Prof. Koichiro Oshima)
2009 M.S. in Graduate School of Engineering Kyoto University (Prof. Koichiro Oshima)
2010–2011 Visiting Student at California Institute of Technology (Prof. Brian M. Stoltz)
2012 Ph.D. in Graduate School of Engineering, Kyoto University (Prof. Seijiro Matsubara, Prof. Koichiro Oshima, and Prof. Hideki Yorimitsu)
2009–2012 Research Fellow of the JSPS (DC1)
2012–2013 Research Fellow of the JSPS (PD), Graduate School of Engineering/Institute of Transformative Bio-Molecules, Nagoya University (Prof. Takashi Ooi)
2013-2014 Assistant Professor, The Hakubi Center for Advanced Research / Department of Chemistry, Graduate School of Science, Kyoto University (Profs. Hideki Yorimitsu, Atsuhiro Osuka)
2014-2016 Assistant Professor, Research Center for Materials Science, Nagoya University (Prof. Kenichiro Itami)
2016-present Associate Professor, Institute of Transformative Bio-Molecules, Nagoya University (Prof. Kenichiro Itami)

【Awards】

2020. The Chemical Society of Japan Award for Young Chemists
2019. Chemical Society of Japan Lecture Award for Young Chemists
2019. The 13th Wakashachi Young Scientists’ Award
2018. The Maruyama Memorial Research Award
2018. Akasaki Award
2016. ITbM Award
2015. Takeda Pharmaceutical Company Award in Synthetic Organic Chemistry, Japan
2014. CSJ Presentation Award 2014
2013. Kyoto University Hakubi researcher
2012. The Reaxys PhD Prize 2012 finalist
2012. CSJ Student Presentation Award 2012
2011. Otsu Academy Award Fellow (No.29)

[Editorial board]
2019〜present Asian Journal of Organic Chemistry (International Advisory Board)

[Original papers]

[42] “Synthesis of Polybenzoacenes: Annulative Dimerization of Phenylene Triflate by Twofold C–H Activation”
Mizuho Uryu,† Taito Hiraga,† Yoshito Koga, Yutaro Saito, Kei Murakami,* Kenichiro Itami*
Angew. Chem., Int. Ed. 2020, Accepted articles. DOI: 10.1002/anie.202001211.

[41] “Roles of Base in the Pd-Catalyzed Annulative Chlorophenylene Dimerization”
Li-Ping Xu, Brandon E. Haines, Manjaly J. Ajitha, Kei Murakami, Kenichiro Itami*, Djamaladdin G. Musaev*
ACS Catal. 2020, 10, 3059–3073. DOI: 10.1021/acscatal.9b05328.

[40] “Rapid Access to Kinase Inhibitor Pharmacophore by Regioselective C–H Arylation of Thieno[2,3-d]pyrimidine”
Shuya Yamada, Kaylin Nicole Flesch, Kei Murakami,* Kenichiro Itami*
Org. Lett. 2020, 22, 1547–1551. DOI:10.1021/acs.orglett.0c00143.

[39] “Dehydrogenative Synthesis of 2,2′-Bipyridyls through Regioselective Pyridine Dimerization”
Shuya Yamada, Takeshi Kaneda, Phillip Steib, Kei Murakami,* Kenichiro Itami*
Angew. Chem., Int. Ed. 2019, 58, 8341–8345. DOI:10.1002/anie.201814701.

[38] “Annulative Synthesis of Benzofurans from General Alkenyl Sulfoxides and Phenols via Pummerer/Sigmatropic Cascade”
Mitsuki Hori, Tomoyuki Yanagi, Kei Murakami, Keisuke Nogi, Hideki Yorimitsu*
Bull. Chem. Soc. Jpn. 2019, 92, 302–311. DOI:10.1246/bcsj.20180321.

[37] “Sigmatropic Dearomatization/Defluorination Strategy for C‐F Transformation: Synthesis of Fluorinated Benzofurans from Polyfluorophenols”
Koichi Okamoto, Mitsuki Hori, Tomoyuki Yanagi, Kei Murakami, Keisuke Nogi, Hideki Yorimitsu*
Angew. Chem. Int. Ed. 2018, 57, 14230–14234. DOI: 10.1002/anie.201809035.

[36] “Gold-Catalyzed C-H Imidation of Polycyclic Aromatic Hydrocarbons”
Yip Shu Jan, Takahiro Kawakami, Kei Murakami,* Kenichiro Itami*
Asian J. Org. Chem. 2018, 7, 1372–1375. DOI: 10.1002/ajoc.201800293.

[35] “Late-Stage Functionalization of Arylacetic Acids by Photoredox-Catalyzed Decarboxylative Carbon–Heteroatom Bond Formation”
Yota Sakakibara, Eri Ito, Tomohiro Fukushima, Kei Murakami,* Kenichiro Itami*
Chem. Eur. J. 2018, 24, 9254–9258 DOI:10.1002/chem.201802143.

[34] “Photoredox-Catalyzed Decarboxylative Oxidation of Arylacetic Acids”
Yota Sakakibara, Phillippa Cooper, Kei Murakami,* Kenichiro Itami*
Chem. Asian J. 2018, Early view. DOI:10.1002/asia.201800529.

[33] “Synthesis of α-Fluoroimines by Copper-Catalyzed Reaction of Diarylacetylenes and N-Fluorobenzenesulfonimide”
Shu Jan Yip, Tetsushi Yoshidomi, Kei Murakami,* Kenichiro Itami*
Chem. Lett. 2018, 47, 329–331. DOI: https://doi.org/10.1246/cl.171097

[32] “Synthesis of partially and fully fused polyaromatics by annulative chlorophenylene dimerization”
Yoshito Koga, Takeshi Kaneda, Yutaro Saito, Kei Murakami,* Kenichiro Itami*
Science 2018, 359, 435–439. DOI: 10.1126/science.aap9801【detail】
Highlighted in …
Chunichi Shimbun, NHK, NIKKAN KOGYO SHIMBUN, Asahi Shimbun, Nikkei Shimbun, C&EN, Kagaku Shimbun 他

 

[31] “Direct Coupling of Naphthalene and Sulfonimides Promoted by DDQ and Blue Light”
Yota Sakakibara†, Eri Ito†, Takahiro Kawakami, Shuya Yamada, Kei Murakami,* Kenichiro Itami* (†Equal contribution)
Chem. Lett. 2017, 46, 1014–1016. DOI: http://dx.doi.org/10.1246/cl.170321

[30] “Catalytic Dehydrogenative C–H Imidation of Arenes Enabled by Photo-generated Hole Donation to Sulfonimide”
Eri Ito, Tomohiro Fukushima, Takahiro Kawakami, Kei Murakami,* Kenichiro Itami*
Chem 2017, 2, 383–392.
[Selected as cover picture]

[29] “Cu-Catalyzed aromatic C–H imidation with N-fluorobenzenesulfonimide: mechanistic details and predictive models”
Brandon E. Haines, Takahiro Kawakami, Keiko Kuwata, Kei Murakami, Kenichiro Itami* and Djamaladdin G. Musaev*
Chem. Sci. 2017, 8, 988–1001.
[Highlighted in C&EN news.]

[28] “Palladium-Catalyzed Cross-Coupling of Aryl Chlorides with Arylsilatranes”
Yutaro Yamamoto, Alexandre Baralle, Anaïs Godefroy, Kei Murakami, Hideki Yorimitsu,* and Atsuhiro Osuka
Heterocycles 2017, 95, 568－574.

[27] “Metal-Free Approach to Biaryls from Phenols and Aryl Sulfoxides by Temporarily Sulfur-Tethered Regioselective C-H/C-H Coupling”
Tomoyuki Yanagi, Yuko Kasuga, Shinya Otsuka, Keisuke Fujimoto, Kei Murakami, Keisuke Nogi, Hideki Yorimitsu,* and Atsuhiro Osuka
J. Am. Chem. Soc. 2016, 138, 14582–14585.

[26] “Regiodivergent Cross-Dehydrogenative Coupling of Pyridines and Benzoxazoles: Discovery of Organic Halides as Regio-Switching Oxidants”
Shuya Yamada, Kei Murakami, and Kenichiro Itami*
Org. Lett. 2016, 18, 2415–2418.

[25]”Palladium-catalyzed C–H Arylation of Pyridines with Aryl Triflates”
Jiao Jiao, Kei Murakami, and Kenichiro Itami*
Chem. Lett. 2016, 45, 529-531.

[24]”Catalytic C–H Imidation of Aromatic Cores of Functional Molecules: Ligand-Accelerated Cu Catalysis and Application to Materials- and Biology-Oriented Aromatics”
Takahiro Kawakami, Kei Murakami, and Kenichiro Itami*
J. Am. Chem. Soc. 2015, 137, 2460–2463.
[Most Read Articles in February 2015]

[22]”Nickel–NHC-Catalyzed Cross-Coupling of 2-Methylsulfanylbenzofurans with Alkyl Grignard Reagents”
Alexandre Baralle, Shinya Otsuka, Vincent Guérin, Kei Murakami, Hideki Yorimitsu,* Atsuhiro Osuka
Synlett 2015, 26, 327-330.

[21] “Activator-Free Palladium-Catalyzed Silylation of Aryl Chlorides with Silylsilatranes”
Yutaro Yamamoto, Hiroshi Matsubara,* Kei Murakami, Hideki Yorimitsu,* Atsuhiro Osuka
Chem. Asian J. 2015, 10, 219-224.

[20] “Two-step, Practical, and Diversity-Oriented Synthesis of Multisubstituted Benzofurans from Phenols through Pummerer Annulation Followed by Cross-coupling”
Kei Murakami, Hideki Yorimitsu,* Atsuhiro Osuka
Bull. Chem. Soc. Jpn. 2014, 87, 1349-1366.
[Selected Papers]

[19] “Palladium-catalyzed Cross-coupling of Unactivated Aryl Sulfides with Arylzinc Reagents under Mild Conditions”
Shinya Otsuka, Daishi Fujino, Kei Murakami, Hideki Yorimitsu,* Atsuhiro Osuka
Chem. Eur. J. 2014, 20, 13146-13149.
[Highlighted in Synfacts]

[18] “Palladium-Catalyzed Amination of Aryl Sulfides with Anilines”
Tomohiro Sugahara, Kei Murakami,* Hideki Yorimitsu,* Atsuhiro Osuka
Angew. Chem. Int. Ed. 2014, 53, 9329-9333.
[Most Accessed in 7/2014]

[17] “Practical, Modular, and General Synthesis of Benzofurans through Extended Pummerer Annulation/Cross-coupling Strategy”
Kei Murakami, Hideki Yorimitsu,* Atsuhiro Osuka
Angew. Chem. Int. Ed. 2014, 53, 7510–7513.

[16] “Amination of meso-Bromoporphyrins and 9-Haloanthracenes with Diarylamines Catalyzed by Pd-PEPPSI Complex”
Yuko Suzuki, Norihito Fukui, Kei Murakami, Hideki Yorimitsu,* Atsuhiro Osuka*
Asian J. Org. Chem. 2013, 2, 1066−1071.
[Selected as a Cover Picture][Highlighted in Chemistry Views][Most accessed 2013/11-2014/11]

[15] “Practical and Scalable Syntheses of Substituted Ketene Dithioacetal Monoxides”
Kei Murakami, Hideki Yorimitsu,* Atsuhiro Osuka
Bull. Chem. Soc. Jpn. 2013, 86, 1193−1195.

[14] “Demetalation of Metal Porphyrins via Magnesium Porphyrins by Reaction with Grignard Reagents”
Kei Murakami, Yutaro Yamamoto, Hideki Yorimitsu,* Atsuhiro Osuka*
Chem. Eur. J. 2013, 19, 9123−9126.
[Selected as a Cover Picture][Highlighted in Chemistry Views]

[13] “Copper-Catalyzed Extended Pummerer Reactions of Ketene Dithioacetal Monoxides with Alkynyl Sulfides and Ynamides with an Accompanying Oxygen Rearrangement ”
Kei Murakami, Junichi Imoto, Hiroshi Matsubara,* Suguru Yoshida, Hideki Yorimitsu,* Koichiro Oshima*
Chem. Eur. J. 2013, 19, 5625–5630.

[12] “A General Approach to the Basiliolide/Transtaganolide Natural Products: The Total Synthesis of Basiliolide B, epi-8-Basiliolide B, Transtaganolide C, and Transtaganolide D”
Hosea M. Nelson, Kei Murakami, Scott C. Virgil, Brian M. Stoltz*
Angew. Chem. Int. Ed. 2011, 50, 3688–3691.
[Highlighted in Synfacts]

[11] “Synthesis of Tetraorganosilanes: (Chloromethyl)dimethylphenylsilane”
Kei Murakami, Hideki Yorimitsu,* Koichiro Oshima* Checked by Jane Panteleev, Mark Lautens
Org. Synth. 2010, 87, 178–183.

[10]”Rhodium-Catalyzed Arylzincation of Terminal Allenes Providing Allylzinc Reagents and Its Application to Versatile Three-component Coupling Reaction”
Yuji Yoshida, Kei Murakami, Hideki Yorimitsu,* Koichiro Oshima*
J. Am. Chem. Soc. 2010, 132, 8878–8879.
[Selected as SYNFACT of the month in Synfacts]

[9] “Cobalt-Catalyzed Benzylzincation of Alkynes”
Kei Murakami, Hideki Yorimitsu,* Koichiro Oshima*
Chem. Eur. J. 2010, 16, 7688–7691.

[8] “Silver-Catalyzed Benzylation and Allylation of Tertiary Alkyl Bromides with Organozinc Reagents”
Yukihiro Mitamura, Yoshihiro Asada, Kei Murakami, Hidenori Someya, Hideki Yorimitsu,* Koichiro Oshima*
Chem. Asian J. 2010, 5, 1487–1493.

[7] “Copper-Catalyzed Arylation of Chlorosilanes with Grignard Reagents”
Eiji Morita, Kei Murakami, Masayuki Iwasaki, Koji Hirano, Hideki Yorimitsu,* Koichiro Oshima*
Bull. Chem. Soc. Jpn. 2009, 82, 1012–1014.

[6] “Cobalt-Catalyzed Arylzincation of Alkynes”
Kei Murakami, Hideki Yorimitsu,* Koichiro Oshima*
Org. Lett. 2009, 11, 2373–2375.

[5] “Zinc-Catalyzed Nucleophilic Substitution Reaction of Chlorosilanes with Organomagnesium Reagents”
Kei Murakami, Hideki Yorimitsu,* Koichiro Oshima*
J. Org. Chem. 2009, 74, 1415−1417.

[4] “Silver-Catalyzed Transmetalation between Chlorosilanes and Aryl and Alkenyl Grignard Reagents for Synthesis of Tetraorganosilanes”
Kei Murakami, Koji Hirano, Hideki Yorimitsu,* Koichiro Oshima*
Angew. Chem. Int. Ed. 2008, 47, 5833–5835.
[Highlighted in Org. Process Res. Dev.]

[3] “Generation of Rhodium Enolates via Retro-Aldol Reaction and Its Application to Regioselective Aldol Reaction”
Kei Murakami, Hirohisa Ohmiya, Hideki Yorimitsu,* Koichiro Oshima*
Tetrahedron Lett. 2008, 49, 2388–2390.

[2] “Nickel-Catalyzed Carbometalation Reactions of [2-(1-Propynyl)phenyl]methanol with 1-Alkenylmagnesium Reagents”
Kei Murakami, Hirohisa Ohmiya, Hideki Yorimitsu,* Koichiro Oshima*
Chem. Lett. 2007, 36, 1066−1067.

[1] “Chromium-Catalyzed Arylmagnesiation of Alkynes”
Kei Murakami, Hirohisa Ohmiya, Hideki Yorimitsu,* Koichiro Oshima*
Org. Lett. 2007, 9, 1569−1571.
[Highlighted in Synfacts]

[Review and Accounts]

[6] “Polycyclic Arene Synthesis by Annulative π-Extension”
Hideto Ito, Yasutomo Segawa, Kei Murakami, Kenichiro Itami*
J. Am. Chem. Soc., 2019, 141, 3–10. DOI: 10.1021/jacs.8b09232.

[5] “Aromatic C–H amination: a radical approach for adding new functions into biology- and materials-oriented aromatics”
Kei Murakami,* Gregory J. P. Perry, Kenichiro Itami*
Org. Biomol. Chem. 2017, 15, 6071–6075. DOI: 10.1039/C7OB00985B

[4] “C–H Functionalization of Azines”
Kei Murakami,* Shuya Yamada, Takeshi Kaneda, Kenichiro Itami*
Chem. Rev. 2017, 117, 9302–9332.

[3] “Catalytic Methods for Aromatic C–H Amination: An Ideal Strategy for Nitrogen-Based Functional Molecules”
Jiao Jiao, Kei Murakami, Kenichiro Itami*
ACS Catal. 2016, 6, 610-633.

[2] “Aromatic Metamorphosis of Dibenzothiophenes”
Hideki Yorimitsu,* Dhananjayan Vasu, M. Bhanuchandra, Kei Murakami, Atsuhiro Osuka
Synlett 2016, 27, 1765–1774.

[1] “Recent Advances in Transition-Metal-Catalyzed Intermolecular Carbomagesiation and Carbozincation”
Kei Murakami, Hideki Yorimitsu*
Beilstein J. Org. Chem. 2013, 9, 278–302.