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Publication

[Original papers]

[61]"Synthesis of N-β-brominated alkenyl isothiocyanates via dehydrogenation of alkyl
isothiocyanates"
Bumpei Maeda, Ryohei Akiyoshi, Daisuke Tanaka, Kohei Sato, Kei Murakami*
Chem. Commun. 2024, 60, 6015–6018. DOI:
10.1039/D4CC01666A.
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[58] "Functionalized polyamine synthesis with photoredox catalysis
Yuta Makihara, Bumpei Maeda, Ryohei Akiyoshi, Daisuke Tanaka, Kei Murakami*
Chem. Eur. J. 2024, 30, e202304374. DOI:10.1002/chem.202304374.   (Shareable link)
[Preprint] "Switchable quaternary ammonium transformation leading to salinity-tolerance-conferring plant biostimulants"
Takumi Kinoshita, Yota Sakakibara, Tomoko Hirano*, Kei Murakami*
ChemRxiv 2023, DOI:10.26434/chemrxiv-2023-bwm63
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[62] “Chemical inhibition of stomatal differentiation by perturbation of the master-regulatory bHLH heterodimer via an ACT-Like domain”
Ayami Nakagawa+, Krishna Mohan Sepuru+, Shu Jan Yip+, Hyemin Seo, Calvin M. Coffin, Kota Hashimoto, Zixuan Li, Yasutomo Segawa, Rie Iwasaki, Hiroe Kato, Stephanie Kim, Yusuke Aihara, Toshinori Kinoshita, Kenichiro Itami, Soon-Ki Han, Kei Murakami*, Keiko U. Torii* (+ Equal contribution)
Nat. Commun. 2024, 15, 8996. DOI:10.1038/s41467-024-53214-4

プレスリリース(日本語)
[56] "Copper-catalyzed reaction of aziridine for the synthesis of substituted 
imidazolidine and imidazolidinone" 
Kota Hashimoto, Daiki Higuchi, Satoshi Matsubara, Kei Murakami*
Front. Chem. 2023, 11, 1272034. [Invited by Prof. Ohshima]
DOI: 10.3389/fchem.2023.1272034

[55] "Nickel/Photoredox-Catalyzed Decarboxylative Coupling of Aryl Bromides with N-Protected Glycine as an Aminomethyl Source"

Jaehyun Jung, Takumi Kinoshita‡, Yuta Makihara‡, Yota Sakakibara, Kazuma Amaike,

Kei Murakami*, Kenichiro Itami* (‡ Equal contribution)

Synlett 2024, 35, 337–341. DOI: 10.1055/s-0041-1738444

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[54] "Copper-catalyzed heterocyclic recombination of aziridine and diazetidine for the synthesis of imidazolidine"
Daiki Higuchi, Satoshi Matsubara, Hiroki Kadowaki, Daisuke Tanaka, Kei Murakami*

Chem. Eur. J. 2023, 29, e202301071. DOI: 10.1002/chem.202301071
Shareable link

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[53] "Divergent Synthesis of Stachyurin and Casuarinin Focusing on C-Glycosidic Bond Reactivity"
Reina Kusuki, Kei Murakami, Ryo Katsuta, Ken Ishigami, Shinnosuke Wakamori
*
Chem. Eur. J. 2023, 29, e202301096. DOI: 10.1002/chem.202301096

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[52] “Identification and improvement of isothiocyanate-based inhibitors on stomatal opening to act as drought tolerance–conferring agrochemicals”

Yusuke Aihara, Bumpei Maeda, Kanna Goto, Koji Takahashi, Mika Nomoto, Shigeo Toh, Wenxiu Ye, Yosuke Toda, Mami Uchida, Eri Asai, Yasuomi Tada, Kenichiro Itami, Ayato Sato, Kei Murakami*, Toshinori Kinoshita*

Nature Comm. 2023, 14, 2665. DOI:10.1038/s41467-023-38102-7

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[51] "Synthesis of α-substituted alkenylammonium salts through Suzuki–Miyaura and Sonogashira coupling"

Aoi Yoshita, Yota Sakakibara, Kei Murakami*

Bull. Chem. Soc. Jpn. 2023, 96, 303–305. DOI:10.1246/bcsj.20230018 [Open Access]

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[50] "Verification of Biaryl-Structure Axial Chirality Produced in Ellagitannins by Chemical Oxidation"

Shinnosuke Wakamori*,Rumi Osada, Shintaro Matsumoto, Reina Kusuki, Kei Murakami

Org, Lett. 202224, 8130–8135. DOI:10.1021/acs.orglett.2c03173

images_large_ol2c03173_0008.jpeg

[49] “Photoinduced Synthesis of Thiocyanates through Hydrogen Atom Transfer and One-Pot Derivatization to Isothiocyanates”

Bumpei Maeda, Yusuke Aihara, Ayato Sato, Toshinori Kinoshita, Kei Murakami*

Org. Lett. 2022, 24, 7366–7371. DOI:10.1021/acs.orglett.2c02896.

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[48] “Identification of stomatal-regulating molecules from de novo arylamine collection through aromatic C–H amination”

Yosuke Toda,* Gregory J. P. Perry,† Shimpei Inoue,† Eri Ito,† Takahiro Kawakami, Mina R. Narouz, Koji Takahashi, Yusuke Aihara, Bumpei Maeda, Toshinori Kinoshita, Kenichiro Itami, Kei Murakami* (†Equal contribution)

Sci. Rep. 2022, 12, 949. DOI:10.1038/s41598-022-04947-z.

[47] “C–H Acyloxylation of Polycyclic Aromatic Hydrocarbons”

Yota Sakakibara, Kei Murakami,* Kenichiro Itami*

Org. Lett. 2022, 24, 602–607. DOI:/10.1021/acs.orglett.1c04030.

[46] “Photoredox-Catalyzed Benzylic Esterification via Radical-Polar Crossover”

Bumpei Maeda, Yota Sakakibara, Kei Murakami,* Kenichiro Itami* (†Equial contribution)

Org. Lett. 2021, 23, 5113–5117. Doi/10.1021/acs.orglett.1c01645 

[45] "Discovery of bactericides as an acute mitochondrial membrane damage inducer"

Ryan Houston, Yusuke Sekine, Mads B. Larsen, Kei Murakami, Steven J. Mullett, Stacy G. Wendell, Derek P. Narendra, Bill B. Chen, Shiori Sekine*

Mol. Biol. Cell 2021, 32, 21. DOI: 10.1091/mbc.E21-04-0191

[44] “Photo-induced arylation of carbazoles with aryldiazonium salts”

Bumpei Maeda, Genki Mori, Yota Sakakibara, Akiko Yagi, Kei Murakami,* Kenichiro Itami*
Asian J. Org. Chem. 2021, 10, 1428-1431. DOI: 10.1002/ajoc.202100191
Shareable link

[43] “Creation of negatively curved polyaromatics enabled by annulative coupling that forms an eight-membered ring”

Satoshi Matsubara,† Yoshito Koga,† Yasutomo Segawa, Kei Murakami,* Kenichiro Itami* (†Equial contribution)

Nature Catalysis 2020, 3, 710–718. DOI: 10.1038/s41929-020-0487-0.

[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* (†Equial contribution)

Angew. Chem., Int. Ed. 2020, 59, 6551–6554. 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, Philip 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. [Open Access]

[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, 13, 2410–2413. 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 [Open Access]

[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

[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 [Open Access]

[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. [OPEN ARCHIVE]

[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.

[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. [Open Access]

[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.

[23]”Transition-Metal-Free Synthesis of Carbazoles and Indoles by an SNAr-Based “Aromatic Metamorphosis” of Thiaarenes”

M. Bhanuchandra, Kei Murakami, Dhananjayan Vasu, Hideki Yorimitsu* and Atsuhiro Osuka

Angew. Chem. Int. Ed. 2015, 54, 10234–10238.

[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, 327330.

[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, 219224.

[20] “Two-step, Practical, and Diversity-Oriented Synthesis of Multisubstituted Benzofurans from Phenols through Pummerer Annulation Followed by Cross-coupling” [Open access]

Kei Murakami, Hideki Yorimitsu,* Atsuhiro Osuka

Bull. Chem. Soc. Jpn. 2014, 87, 13491366. [Open Access]

[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.

[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.

[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.

[15] “Practical and Scalable Syntheses of Substituted Ketene Dithioacetal Monoxides”

Kei Murakami, Hideki Yorimitsu,* Atsuhiro Osuka

Bull. Chem. Soc. Jpn. 2013, 86, 1193−1195. [Open Access]

[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.

[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.

[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.

[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. [Open Access]

[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.

[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. [Open Access]

[1] “Chromium-Catalyzed Arylmagnesiation of Alkynes”

Kei Murakami, Hirohisa Ohmiya, Hideki Yorimitsu,* Koichiro Oshima*

Org. Lett. 2007, 9, 1569−1571.

[57] "Switchable Decarboxylation by Energy- or Electron-Transfer Photocatalysis"
Yota Sakakibara, Kenichiro Itami, Kei Murakami*
J. Am. Chem. Soc. 2024, 146, 1554–1562. DOI:10.1021/jacs.3c11588
Spotlight Research: https://www.chem-station.com/blog/2024/01/eetp.html
Press Release: https://www.kwansei.ac.jp/news/detail/5049
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[59]"Photoinduced dehydrogenation of protected piperazines"
Kokoro Nowaki, Bumpei Maeda, Kei Murakami*
Chem. Lett. 2024, 53, uape024.
DOI:10.1093/chemle/upae024

[60]"Photoredox-Enabled Synthesis of α-Alkylated Alkenylammonium Salts"

Rina Tonedachi, Aoi Yoshita, Yota Sakaibara*, Kei Murakami*

Synthesis 2024, 35, 337–341. [Selected on the cover]

DOI:10.1055/a-2302-5887

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Orignal pepers

[Review & Accounts]

[11] "Recent Advancement in the Synthesis of Isothiocyanates "
Bumpei Ma
eda, Kei Murakami*
Chem. Commun. 2024, 60, 2839–2864. DOI:10.1039/D3CC06118C
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[10] "Divergent Transformation of Carboxylic Acids through Photocatalytic Decarboxylation with Hypervalent Iodine Reagents"
Yota Sakakibara, Kenichiro Itami, Kei Murakami*
J. Synth. Org. Chem., Jpn. 2023, 81, 1050-1061. [Open Access]
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[9] “Development of annulative coupling and aromatic amination toward the synthesis of structurally new aromatic amines”
Kei Murakami*

Bull. Chem. Soc. Jpn. 2023, 96, 591–600. [Open Access]

[8] "Switchable Divergent Synthesis Using Photocatalysis"
Yota Sakakibara, Kei Murakami*

ACS Catal. 2022, 12, 1857–1878. DOI/10.1021/acscatal.1c05318

[7]“Synthesis of octagon-containing molecular nanocarbons”
Greco González Miera, Satoshi Matsubara, Hideya Kono, Kei Murakami,* Kenichiro Itami*

Chem. Sci. 2022, 13, 1848–1868. DOI:/10.1039/D1SC05586K.

[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. [Open Access]
Review and Accounts
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