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List of Publications Youhei Takeda

As of April 7, 2020

Original Papers 1. “Effect of Alkyl Groups in Pyrene Chromophore on Mechanical Response of

Pyrene-Octafluoronaphthalene Co-Crystals” Iwasaki, T.*; Murakami, S.; Takeda, Y.; Tohnai, N.; Kambe, N. Chem. Asian J. 2020, Early View [DOI: 10.1002/asia.202000138] https://doi.org/10.1002/asia.202000138

2. “Thermally Activated Delayed Fluorescent Donor–Acceptor–Donor–Acceptor p-Conjugated Macrocycle

for Organic Light-Emitting Diodes” Izumi, S.; Higginbotham, H. F.; Nyga, A.; Stachelek, P.; Tohnai, N.; de Silva, P.; Data, P.*; Takeda, Y.*; Minakata, S.* J. Am. Chem. Soc. 2020, 142, 1482–1491. [DOI: 10.1021/jacs.9b11578] https://doi.org/10.1021/jacs.9b11578 an open-access article Press Release (Osaka University, January 8, 2020) Highlighted in ResOU, Optronics, fabcross for エンジニア, EurekAlert!, AlphaGalileo, Phys Org, Nanowerk, EE Times Japan, Science Daily, Bioengineer.org, BITS&CHIPS, BrightSurt.com, SciFi Insight.

3. “Molecular Packing and Solid-state Photophysical Properties of 1,3,6,8-Tetraalkylpyrenes”

Iwasaki, T.*; Murakami, S.; Takeda, Y.; Fukuhara, G.; Tohnai, N.; Yakiyama, Y.; Sakurai, H.; Kambe, N.* Chem. Eur. J. 2019, 25, 14817–14825. [DOI: 10.1002/chem.201903224] https://doi.org/10.1002/chem.201903224 Selected as the “Cover Feature” of the issue (Oct 8, 2019).

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4. “Hydrostatic Pressure-Controlled Ratiometric Luminescence Responses of Dibenzo[a,j]phenazine-Cored

Mechanoluminophore” Takeda, Y.*; Mizuno, H.; Okada, Y.; Okazaki, M.; Minakata, S.; Penfold, T.*; Fukuhara, G.* ChemPhotoChem 2019, 3, 1203–1211. [DOI: 10.1002/cptc.201900190] https://doi.org/10.1002/cptc.201900190 Selected as the “Front Cover” of the issue (December 12, 2019).

5. “Catalyst-Controlled Regiodivergent Ring-Opening C(sp3)–Si Bond-Forming Reactions of 2-Arylaziridines

with Silylborane Enabled by Synergetic Palladium/Copper Dual Catalysis” Takeda, Y.*; Shibuta, K.; Aoki, S.; Tohnai, N.; Minakata, S.* Chem. Sci. 2019, 10, 8642–8647. [DOI: 10.1039/C9SC02507C] https://doi.org/10.1039/C9SC02507C an open-access article

6. “Asymmetric Synthesis of b2-Aryl Amino Acids through Pd-Catalyzed Enantiospecific and Regioselective

Ring-Opening Suzuki-Miyaura Arylation of Aziridine-2-carboxylates” Takeda, Y.*; Matsuno, T.; Sharma, A. K.; Sameera, W. M. C.*; Minakata, S.* Chem. Eur. J. 2019, 25, 10226–10231. [DOI: 10.1002/chem.201902009] https://doi.org/10.1002/chem.201902009 Highlighted in Synfacts 2019, 15, 1076.

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7. “Thermally Activated Delayed Fluorescence vs. Room Temperature Phosphorescence by Conformation

Control of Organic Single Molecules” Data, P.*; Okazaki, M.; Minakata, S.; Takeda, Y.* J. Mater. Chem. C 2019, 7, 6616–6621. [DOI: 10.1039/C9TC00909D] https://doi.org/10.1039/C9TC00909D Invited as the part of the themed collection “Functional Organic Materials for Optoelectronic Applications”.

8. “A Computational Study on the Mechanism and Origin of the Regioselectivity and Stereospecificity in

Pd/SIPr-Catalyzed Ring-Opening Cross-Coupling of 2-Arylaziridines with Arylboronic Acids” Sharma, A. K.; Sameera, W. M. C.*; Takeda, Y.; Minakata, S. ACS Catal. 2019, 9, 4582–4592 [DOI: 10.1021/acscatal.9b01191] https://doi.org/10.1021/acscatal.9b01191

9. “Ni(II) 10-Phosphacorrole: A Porphyrin Analogue Containing Phosphorus at the Meso Position”

Omori, H.; Hiroto, S.; Takeda, Y.; Fliegl, H.; Minakata, S.; Shinokubo, H.* J. Am. Chem. Soc. 2019, 141, 4800–4805. [DOI: 10.1021/jacs.8b13169] https://doi.org/10.1021/jacs.8b13169

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10. “The Impact of Replacement of Nitrogen with Phosphorus Atom in the Pyromellitic Diimides on Their Photophysical and Electrochemical Properties” Pluczyk, S.*; Higginbotham, H.*; Data, P.; Takeda, Y.*; Minakata, S. Electrochim. Acta 2019, 295, 801–809. [DOI: 10.1016/j.electacta.2018.10.156] https://doi.org/10.1016/j.electacta.2018.10.156

11. “Syntheses of Diverse Donor-Substituted Bisbenzofuro[2,3-b:3’,2’-e]pyridines (BBZFPys) via Pd Catalysis,

and Their Photophysical Properties” Itai, Y.; Nishii, Y.; Stachelek, P.; Data, P.*; Takeda, Y.*; Minakata, S.; Miura, M.* J. Org. Chem. 2018, 83, 10289–10302. [DOI: 10.1021/acs.joc.8b01451] https://doi.org/10.1021/acs.joc.8b01451

12. “Conformationally-Flexible and Moderately Electron-Donating Units-Installed D-A-D Triad Enabling

Multi-Color-Changing Mechanochromic Luminescence, TADF and Room-Temperature Phosphorescence” Takeda, Y.*; Kaihara, T.; Okazaki, M.; Higginbotham, H.; Data, P.*; Tohnai, N.; Minakata, S. Chem. Commun. 2018, 54, 6847–6850. [DOI: 10.1039/c8cc02365d] https://doi.org/10.1039/c8cc02365d an open-access article Invited as the part of the themed collection “Chem Commun 2018 Emerging Investigators”. Selected as an Emerging Investigator 2018.

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13. “FRET-Mediated Near Infrared Whispering Gallery Modes: Studies on the Relevance of Intracavity Energy Transfer with Q-Factor” Oki, O.; Kushida, S.; Mikosch, A.; Hatanaka, K.; Takeda, Y.; Minakata, S.; Kuwabara, J.; Kanbara, T.; Dao, T. D.; Ishii, S.; Nagao, T.; Kuehne, A. J. C.; Deschler, F.; Friend, R.; Yamamoto, Y.* Mater. Chem. Front. 2018, 2, 270–274. [DOI: 10.1039/C7QM00498B] https://doi.org/10.1039/C7QM00498B Invited as the part of the themed collection “Pi conjugated system bricolage (figuration) toward functional organic molecular systems”.

14. “An Optical and Electrical Study of Fully Thermally Activated Delayed Fluorescent White Organic

Light-emitting Diodes” Pereira, D.*; Santos, P. L.; Ward, J.; Data, P.; Okazaki, M.; Takeda, Y.; Minakata, S.; Bryce, M.; Monkman, A. P. Sci. Rep. 2017, 7, 6234/1–8. [DOI: 10.1038/s41598-017-06568-3] https://doi.org/10.1038/s41598-017-06568-3 an open-access article

15. “Thermally Activated Delayed Fluorescent Phenothiazine-dibenzo[a,j]phenazine-phenothiazine Triads Exhibiting Tricolor-Changing Mechanochromic Luminescence” Okazaki, M.; Takeda, Y.*; Data, P.*; Pander, P.; Higginbotham, H.; Monkman, A. P.; Minakata, S.* Chem. Sci. 2017, 8, 2677–2686. [DOI: 10.1039/C6SC04863C] https://doi.org/10.1039/C6SC04863C an open-access article Press Release (Osaka University, January 13, 2017) Highlighted in ResOU, Chem-Station, AlphaGalileo, EurekAlert!, ScienceDaily, Phys Org, Optronics, UPI, Asian Scientist, and American Laboratory, and Kodomo-no-Kagaku. Ranked in the most downloaded Chemical Science articles of 2017 (within top 7 in Inorganic and Physical Chemistry field) Ranked in one of the top 5% of authors, highly cited in the Royal Society of Chemistry journals in 2019.

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16. “Oxidative Self-annulation of 2,5-Diaryl-3,4-diaminothiophene via C–C and C–S Bond Cleavage of the

Thiophene Ring: A New Synthesis of An Amino-substituted Triarylthieno[3,4-b]pyrazines and Their Photophysical Properties” Takeda, Y.*; Ueta, S.; Minakata, S.* Heterocycles 2017, 95, 137–144. (Professor Masakatsu Shibasaki’s Special Issues) [DOI: 10.3987/COM-16-S(S)11] https://doi.org/10.3987/COM-16-S(S)11

17. “Palladium-Catalyzed Regioselective and Stereo-invertive Ring-Opening Borylation of 2-Arylaziridines

with Bis(pinacolato)diboron: Experimental and Computational Studies” Takeda, Y.*; Kuroda, A.; Sameera, W. M. C.; Morokuma, K.*; Minakata, S.* Chem. Sci. 2016, 7, 6141–6152. [DOI: 10.1039/C6SC01120A] https://doi.org/10.1039/C6SC01120A an open-access article Highlighted in J. Synth. Org. Chem. Jpn.

18. “Thieno[3,4-c]phosphole-4,6-dione: A Versatile Building Block for Phosphorus-containing Functional

p-Conjugated Systems” Takeda, Y.*; Hatanaka, K.; Nishida, T.; Minakata, S.* Chem. Eur. J. 2016, 22, 10460–10364. [DOI: 10.1002/anie.201602392] https://doi.org/10.1002/anie.201602392 Highlighted in Atlas of Science (October 7, 2016).

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19. “Dibenzo[a,j]phenzine-Cored Donor-Acceptor-Donor (D-A-D) Compounds as Green-to-Red/NIR

Thermally Activated Delayed Fluorescence Organic Light Emitters” Data, P.*; Pander, P.; Okazaki, M.; Takeda, Y.*; Minakata, S.; Monkman, A. P. Angew. Chem., Int. Ed. 2016, 55, 5739–5744. [DOI: 10.1002/anie.201600113] https://doi.org/10.1002/anie.201600113 Press Release (Osaka University, April 7, 2016) Highlighted in a newspaper (The Science News, April 29, 2016). Highlighted in ResOU, AlphaGalileo, EurekAlert!, ScienceDaily, Materials Today, Phys Org, and Optronics.

20. “Ring-Contractive and –Closing Skeletal Rearrangement of 1,1’-Binaphthalene-2,2’-Diamines (BINAMs) Induced by an Iodine-containing Oxidant: Synthesis of Spiro[benzo[e]indole-1,1’-inden]-2-amines and Application to an AIEE-active BF2 Complex” Okazaki, M.; Takahashi, K.; Takeda, Y.*; Minakata, S.* Heterocycles 2016, 93, 770–782. (Professor Lutz F. Tietze’s Special Issues) [DOI: 10.3987/COM-15-S(T)33] https://doi.org/10.3987/COM-15-S(T)33

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21. “A Facile Synthesis of Functionalized 7,8-Diaza[5]helicenes through an Oxidative Ring-closure of 1,1’-Binaphthalene-2,2’-diamines (BINAMs)” Takeda, Y.*; Okazaki, M.; Maruoka, Y.; Minakata, S.* Beilstein J. Org. Chem. 2015, 11, 9–15. [DOI: 10.3762/bjoc.11.2] https://doi.org/10.3762/bjoc.11.2 an open-access article

22. “2-Halogenoimidazolium Salt Catalyzed Aza-Diels–Alder Reaction through Halogen-Bond Formation” Takeda, Y.*; Hisakuni, D.; Lin, C.-H.; Minakata, S.* Org. Lett. 2015, 17, 318–321. [DOI: 10.1021/ol503426f] https://doi.org/10.1021/ol503426f

23. “Revisiting Phosphorus Analogues of Phthalimides and Naphthalimides: Syntheses and Comparative Studies” Takeda, Y.*; Nishida, T.; Hatanaka, K.; Minakata, S.* Chem.—Eur. J. 2015, 21, 1666–1672. [DOI: 10.1002/chem.201405494] https://doi.org/10.1002/chem.201405494

24. “Oxidative Skeletal Rearrangement of 1,1’-Binaphthalene-2,2’-Diamines (BINAMs) via C–C Bond

Cleavage and Nitrogen Migration: A Versatile Synthesis of U-Shaped Azaacenes” Takeda, Y.*; Okazaki, M.; Minakata, S.* Chem. Commun. 2014, 50, 10291–10294. [DOI: 10.1039/C4CC04911J]

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https://doi.org/10.1039/C4CC04911J an open-access article Highlighted in Synfacts 2014, 10, 1036.

25. “2,6-Diphospha-s-indacene-1,3,5,7(2H,6H)-tetraone: A Phosphorus Analogue of Aromatic Diimides with the Minimal Core Exhibiting High Electron-accepting Ability” Takeda, Y.*; Nishida, T.; Minakata, S.* Chem.—Eur. J. 2014, 20, 10266–10270. [DOI: 10.1002/chem.201403735] https://doi.org/10.1002/chem.201403735

26. “Pd/NHC-Catalyzed Enantiospecific and Regioselective Suzuki-Miyaura Arylation of 2-Arylaziridines:

Synthesis of Enantioenriched 2-Arylphenethylamine Derivatives” Takeda, Y.*; Ikeda, Y.; Kuroda, A.; Tanaka, S.; Minakata, S.* J. Am. Chem. Soc. 2014, 136, 8544–8547. [DOI: 10.1021/ja5039616] https://doi.org/10.1021/ja5039616 Highlighted in “Some Items of Interest to Process R&D Chemists and Engineers” (Org. Process Res. Dev. 2014, 18, 922–927.)

27. “Oxidative Dimerization of (Hetero)aromatic Amines Utilizing t-BuOI Leading to (Hetero)aromatic Azo

Compounds: Scope and Mechanistic Studies” Okumura, S.; Lin, C.-H.; Takeda, Y.*; Minakata, S.* J. Org. Chem. 2013, 78, 12090–12105. [DOI: 10.1021/jo402120w] https://doi.org/10.1021/jo402120w

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28. “PCy3-Catalyzed Ring-Expansion of Aziridinofullerenes with CO2 and Aryl Isocyanates: Evidence for a Two-Consecutive Nucleophilic Substitution Pathway on the Fullerene Cage” Takeda, Y.; Kawai, H.; Minakata, S.* Chem.—Eur. J. 2013, 19, 13479–13483. [DOI: 10.1002/chem.201301617] https://doi.org/10.1002/chem.201301617

29. “Hypervalent Iodine(III)-Induced Oxidative [4+2] Annulation of o-Phenylenediamines and Electron-Deficient Alkynes: Direct Synthesis of Quinoxalines from Alkyne Substrates under Metal-Free Conditions” Okumura, S.; Takeda, Y.*; Kiyokawa, K.; Minakata, S.* Chem. Commun. 2013, 49, 9266–9268. [DOI: 10.1039/C3CC45469J] https://doi.org/10.1039/C3CC45469J an open-access article Highlighted in Synfacts 2014, 38.

30. “A Practical Synthesis of Azobenzenes through Oxidative Dimerization of Aromatic Amines Using tert-Butyl Hypoiodite” Takeda, Y.; Okumura, S.; Minakata, S.* Synthesis 2013, 45, 1029–1033. [DOI: 10.1055/s-0032-1318388] https://doi.org/10.1055/s-0032-1318388 Invited as a “PSP(Practical Synthetic Procedures)-article”.

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31. “Straightforward and Versatile Synthesis of Fullerooxazoles from C60 and Carboxamides through Radical

Reactions under Mild Conditions” Takeda, Y.; Enokijima, S.; Nagamachi, T.; Nakayama, K.; Minakata, S.* Asian J. Org. Chem. 2013, 2, 91–97. [DOI: 10.1002/ajoc.201200114] https://doi.org/10.1002/ajoc.201200114 Selected as the “Cover Picture” of the issue (Jan 10, 2013). Highlighted in ChemistryViews as a “Noteworthy Paper” (Oct 23, 2012). Highlighted in “ワイリー・サイエンスカフェ” (Oct 23, 2012). Ranked as the most-accessed article for February, March, April and May 2013 in a row.

32. “An Inclusion Complex of C60 with Organosilylated g-Cyclodextrin: Drastic Enhancement of Apparent

Solubility of C60 in Nonpolar and Weakly Polar Organic Solvents” Takeda, Y.; Nagamachi, T.; Nishikori, K.; Minakata, S.* Asian J. Org. Chem. 2013, 2, 69–73. [DOI: 10.1002/ajoc.201200160] https://doi.org/10.1002/ajoc.201200160 Highlighted in ChemistryViews as a “Noteworthy Paper” (Jan 7, 2013). Highlighted in “ワイリー・サイエンスカフェ” (Jan 7, 2013). Highlighted in “Angewandte Spotlights” (Angew. Chem. Int. Ed. 2013, 52, 796–798.) Ranked as one of the most-accessed articles (6th) for February 2013.

33. “Transition-metal-free Benzylic C–H Bond Intermolecular Amination Utilizing Chloramine-T and I2”

Takeda, Y.; Hayakawa, J.; Yano, K.; Minakata, S.* Chem. Lett. 2012, 41, 1672–1674. [DOI: 10.12461/cl.2012.1672] https://doi.org/10.12461/cl.2012.1672

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34. “Nucleophilic Ring-Opening of N-o-Nosylaziridines with N-Chloro-N-Sodiocarbamate: Facile Preparation of Differentially Protected Vicinal Diamines” Takeda, Y.; Murakami, Y.; Ikeda, Y.; Minakata, S.* Asian J. Org. Chem. 2012, 1, 226–230. [DOI: 10.1002/ajoc.201200070] https://doi.org/10.1002/ajoc.201200070

35. “Cyclizative Atmospheric CO2 Fixation by Unsaturated Amines with t-BuOI Leading to Cyclic Carbamates” Takeda, Y.; Okumura, S.; Tone, S.; Sasaki, I.; Minakata, S.* Org. Lett. 2012, 14, 4874–4877. [DOI: 10.1021/ol302201q] https://doi.org/10.1021/ol302201q Highlighted in “Noteworthy Chemistry” (October 1, 2012).

36. “Selective Functionalization of Fullerenes with N,N-Dihalosulfonamides as an N1 Unit: Versatile Syntheses

of Aza[60]fulleroids and Aziridino[60]fullerenes and their Application to Photovoltaic Cells” Nagamachi, T.; Takeda, Y.; Nakayama, K.; Minakata, S.* Chem.—Eur. J. 2012, 18, 12035–12045. [DOI: 10.1002/chem.201201680] https://doi.org/10.1002/chem.201201680

37. “An Air-stable Low-Bandgap n-Type Organic Polymer Semiconductor Exhibiting Selective Solubility in Perfluorinated Solvents”

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Takeda, Y.; Andrew, T. L.; Lobez, J. M.; Mork, A. J.; Swager, T. M.* Angew. Chem., Int. Ed. 2012, 51, 9042–9046. [DOI: 10.1002/anie.201204066] https://doi.org/10.1002/anie.201204066

38. “Oxidative Dimerization of Aromatic Amines Using t-BuOI: Entry to Unsymmetric Aromatic Azo

Compounds” Takeda, Y.; Okumura, S.; Minakata, S.* Angew. Chem., Int. Ed. 2012, 51, 7804–7808. [DOI: 10.1002/anie.201202786] Selected as a “Hot Paper” (July 4, 2012). Highlighted in “ワイリー・サイエンスカフェ” (July 4, 2012). Highlighted in “Noteworthy Chemistry” (August 27, 2012). Highlighted in Synfacts 2012, 1091. https://doi.org/10.1002/anie.201202786

39. “1,4-Bis(diarylamino)-2,5-bis(4-cyanophenylethenyl)benzenes: Fluorophores Exhibiting Efficient Red and

Near-Infrared Emissions in Solid State” Shimizu, M.*; Kaki, R.; Takeda, Y.; Hiyama, T.; Nagai, N.; Yamagishi, H.; Furutani, H. Angew. Chem., Int. Ed. 2012, 51, 4095–4099. [DOI: 10.1002/anie.201108943] https://doi.org/10.1002/anie.201108943

40. “Mechanistic Study on the Palladium-catalyzed Stereoselective Cross-coupling Reaction of

1,1-Dibromo-3,3,3-trifluoro-2-tosyloxypropene” Shimizu, M.*; Takeda, Y.; Hiyama, T. Bull. Chem. Soc. Jpn. 2011, 84, 1339–1341. [DOI: 10.1246/bcsj.20110240] https://doi.org/10.1246/bcsj.20110240 Chosen as a BCSJ “Selected Papers” of the issue (December, 2011).

Dateiname: Z202786E Pagina: 6Pfad: L:/daten/Verlage/VCH/ACH/hefte/pool/ Seite: 6 te von 6Status Neusatz Umfang (Seiten): 6Datum: 26 KW., 21. Juni 2012 (Donnerstag) Zeit: 10:46:39 Uhr

CommunicationsSynthetic Methods

Y. Takeda, S. Okumura,S. Minakata* &&&&—&&&&

Oxidative Dimerization of AromaticAmines using tBuOI: Entry toUnsymmetric Aromatic Azo Compounds

It’s all the hype : An oxidative dimeriza-tion reaction of aromatic amines utilizingtert-butyl hypoiodite (tBuOI) under mildreaction conditions leads to aromatic azocompounds (see scheme). The method

allows access to unsymmetric aromaticazo compounds, which are difficult toprepare by conventional synthetic meth-ods, in a selective manner.&picture wastoo big&

Synthesemethoden

Y. Takeda, S. Okumura,S. Minakata* &&&&—&&&&

Oxidative Dimerization of AromaticAmines using tBuOI: Entry toUnsymmetric Aromatic Azo Compounds

Hypo hilft : Eine oxidative Dimerisierungvon aromatischen Aminen mit tert-Butyl-hypoiodit (tBuOI) unter milden Reak-tionsbedingungen f!hrt zu aromatischenAzoverbindungen (siehe Schema). Die

Reaktion bietet selektiven Zugang zuunsymmetrischen aromatischen Azover-bindungen, die durch herkçmmlicheSynthesemethoden schwer herzustellensind.

.AngewandteCommunications

6 www.angewandte.org ! 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Angew. Chem. Int. Ed. 2012, 51, 1 – 6! !

These are not the final page numbers!

1 12 23 34 45 56 67 78 89 9

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41. “Twisting Strategy Applied to N,N-Diorganoquinacridones Leads to Organic Chromophores Exhibiting

Efficient Solid-state Fluorescence” Shimizu, M.*; Asai, Y.; Takeda, Y.; Yamatani, A.; Hiyama, T. Tetrahedron Lett. 2011, 52, 4084–4089. [DOI: 10.1016/j.tetlet.2011.05.087] https://doi.org/10.1016/j.tetlet.2011.05.087

42. “Synthesis and Photophysical Properties of Dimethoxybis(3,3,3-trifluoropropen-1-yl)benzenes: Compact

Chromophores Exhibiting Violet Fluorescence in the Solid State” Shimizu, M.*; Takeda, Y.; Higashi, M.; Hiyama, T. Chem.—Asian J. 2011, 6, 2536–2544. [DOI: 10.1002/asia.201100176] https://doi.org/10.1002/asia.201100176

43. “Diastereoselective Aziridination of Chiral Electron-deficient Olefins with N-Chloro-N-sodio-

carbamates Catalyzed by Chiral Quaternary Ammonium Salts” Murakami, Y.; Takeda, Y.; Minakata, S.* J. Org. Chem. 2011, 76, 6277–6285. [DOI: 10.1021/jo2010632] https://doi.org/10.1021/jo2010632

44. “Generation of Nitrile Oxides from Oximes Using t-BuOI and Their Cycloaddition”

Minakata, S.*; Okumura, S.; Nagamachi, T.; Takeda, Y. Org. Lett. 2011, 13, 2966–2969. [DOI: 10.1021/ol2010616] https://doi.org/10.1021/ol2010616 Ranked in “the top 20 most downloaded articles” of May 2011.

BULLETINOF THE

CHEMICAL SOCIETY OF JAPAN

Selected PapersMechanistic Study of the Palladium-CatalyzedStereoselective Cross-Coupling Reaction of1,1-Dibromo-3,3,3-trifluoro-2-tosyloxypropene

We prepared a Pd complex by the oxidative addition of 1,1-dibromo-3,3,3-trifl uoro-2-tosyloxypropene to [Pd(PPh3)4 ]. The atomic distance between Pd andF in the complex was 2.95 ¡, which was shorter than the sum of the van derWaals radii. Based on NMR studies of the oxidative addition step, a catalyticcycle for the Pd-catalyzed cross-coupling reaction of the propene is proposed,with the Pd­F interaction as the key element for the Z-selectivity.

TsO

F3C Ph

BrTsO

Pd

Br

FFF

Br

PPh 3

Ph 3 P

TsO

F3C Br

Br

[Pd(PPh 3 )4 ](5 mol%) PhB(OH)2

Z /E = ca. 9 : 1

aq. Cs2 CO3toluene

Masaki Shimizu,* Youhei Takeda,and Tamejiro Hiyama

Bull. Chem. Soc. Jpn.1–3

BULLETIN 2011/11/16 20110240 (OB)

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45. “New Preparation and Synthetic Reactions of 3,3,3-Trifluoropropynyllithium, -borate and -stannane: Facile

Synthesis of Trifluoromethylated Allenes, Arylacetylenes and Enynes” Shimizu, M.*; Higashi, M.; Takeda, Y.; Murai, M.; Jiang, G.; Asai, Y.; Nakao, Y.; Shirakawa, E.; Hiyama, T. Future Med. Chem. 2009, 1, 921–945. [DOI: 10.4155/fmc.09.69] https://doi.org/10.4155/fmc.09.69

46. “1,4-Bis(alkenyl)-2,5-dipiperidinobenzenes: Minimal Fluorophores Exhibiting Highly Efficient Emission in the Solid State” Shimizu, M.*; Takeda, Y.; Higashi, M.; Hiyama, T. Angew. Chem., Int. Ed. 2009, 48, 3653–3656. [DOI: 10.1002/anie.200900963] https://doi.org/10.1002/anie.200900963 Highlighted in “Noteworthy Chemistry” May 4, 2009. Highlighted in Synfacts 2009, 734. Highlighted in Biotechnol. J. 2009, 4, 791–792.

47. “Preparation, Structure, and Diels–Alder Reaction of Phenyl(trifluoromethanesulfonate)- (3,3,3-trifluoropropynyl)-l3-iodane” Shimizu, M.*; Takeda, Y.; Hiyama, T. Chem. Lett. 2008, 37, 1304–1305. [DOI: 10.1246/cl.2008.1304] https://doi.org/10.1246/cl.2008.1304

48. “Stereoselective Preparation and Cope Rearrangement of 2-CF3-Cis-2,3-bis(alkenyl)oxiranes: A Facile Route to 2-CF3-Substituted Oxacycles” Shimizu, M.*; Fujimoto, T.; Liu, X.; Takeda, Y.; Hiyama, T. Heterocycles 2008, 76, 329–351. (Professor Ryoji Noyori’s Special Issues) [DOI: 10.3987/COM-08-S(N)13] https://doi.org/10.3987/COM-08-S(N)13

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49. “Straightforward Synthesis of CF3-Substituted Triarylethenes by Stereoselective Threefold Cross-coupling

Reactions” Takeda, Y.; Shimizu, M.*; Hiyama, T. Angew. Chem., Int. Ed. 2007, 46, 8659–8661. [DOI: 10.1002/anie.200703759] https://doi.org/10.1002/anie.200703759 Highlighted in Synfacts 2008, 172.

50. “Novel Generation of 3,3,3-Trifluoropropynyllithium and Transformation of the Carbonyl Adducts to

Trifluoromethyl-substituted Allenes” Shimizu, M.*; Higashi, M.; Takeda, Y.; Jiang, G.; Murai, M.; Hiyama, T. Synlett 2007, 1163–1165. (Cluster issue: Invited Paper) [DOI: 10.1055/s-2007-977422] https://doi.org/10.1055/s-2007-977422

51. “Facile Synthesis of Trifluoromethyl-substituted Enynes: Remarkable Reactivity and Stereoselectivity of

Tributyl(3,3,3-trifluoropropynyl)stannane in Carbostannylation of Alkynes” Shimizu, M.*; Jiang, G.; Murai, M.; Takeda, Y.; Nakao, Y.; Hiyama, T.; Shirakawa, E. Chem. Lett. 2005, 34, 1700–1701. [DOI: 10.1246/cl.2005.1700] https://doi.org/10.1246/cl.2005.1700

Reviews and Accounts 1. “Aromatic-Fused Diketophosphanyl-Core Organic Functional Materials: Phosphorus Mimics of Imides or

Beyond?” (Review) Takeda, Y.*; Minakata, S. Org. Biomol. Chem. 2019, 17, 7807–7821. [DOI: 10.1039/C9OB01328H] https://doi.org/10.1039/C9OB01328H Featured as the part of “Organic & Biomolecular Chemistry HOT article collection”.

R1 R2

+

R1

Bu3Sn

R2

CF3Pd2(dba)3 (1 mol%)t-Bu3P (2 mo%)

toluener.t.

Bu3Sn CF3

single stereoisomer !

17

2. “Recent Advancements in and the Future of Organic Emitters: TADF- and RTP-Active Multifunctional

Organic Materials” (Minireview) Data, P.*; Takeda, Y.* Chem.—Asian J. 2019, 14, 1613–1636. [DOI: 10.1002/asia.201801791] https://doi.org/10.505910.1002/asia.201801791 Invited as the part of the Special Issue “p-Conjugated Compounds for Molecular Materials”. an open-access article

3. “Creation of Novel Functional Aza-Containing p-Conjugated Molecules Based on the Development of Novel Oxidative Transformations of Aromatic Amines” (accounts) Takeda, Y. J. Synth. Org. Chem., Jpn. 2016, 74, 955–964. [DOI: 10.5059/yukigoseikyokaishi.74.955] https://doi.org/10.5059/yukigoseikyokaishi.74.955

Conference Proceedings 1. “Design and Synthesis of Highly Emissive Solid Fluorophores”

Shimizu, M.; Mochida, K.; Takeda, Y.; Asai, Y.; Hiyama, T. Proceedings of SPIE 2009, 7415, 74151G. [DOI: 10.1117/12.825442] https://doi.org/10.1117/12.825442

N

N

EWG

EWGArAr

NH2

NH2

ArNH2

ArNH2

Ar1NH2

N NAr2

N

NH2NN

Ar

Ar

N N

Ar

Ar

Ar

Ar

Novel OxidativeTransformations

of Aromatic Amines

Ar2NH2

Ar1

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Patents 1. “Compositions, Methods, and Systems Comprising Fluorous-soluble Polymers”

Swager, T. M.; Lim, J.; Takeda, Y. U.S. Pat. Appl. Serial No.: 13/213,647 (08/19/2011) Books 1. “Cyclic O,N-Acetals”

Minakata, S.; Takeda, Y. In Science of Synthesis: Knowledge Updates 2019/2; Carreira, E. M., Clarke, P., Drabowicz, J., Murai, T., Reibig, H.-U., Schaumann, E., Terent’ev, A. Eds.; Georg Thieme Verlag KG: Stuttgart, 2019; 30.1.2.3, pp 63–70.

2. “イミノフラーレンの選択的合成反応“ 武田洋平，南方聖司 フラーレン誘導体・内包技術の最前線（松尾 豊監修），シーエムシー出版，2014，第 2 章 4 節, pp 60–69.

3. “N1 Unit Transfer Reaction to C–C Double Bonds” Minakata, S.; Takeda, Y.; Kiyokawa, K. In Methods and Applications of Cycloaddition Reactions in Organic Syntheses, Nishiwaki, N. Ed.; Wiley-VCH: Hoboken, 2014; Chapter 2, pp 67–88.

4. “Heterocyclic Reagents Containing Nitrogen-Halogen Bond: Recent Applications” Minakata, S.; Takeda, Y.; Hayakawa, J. In Halogenated Heterocycles: Synthesis, Application and Environment, Topics in Heterocyclic Chemistry Series, Vol. 27; Iskra, J. Ed.; Springer: Berlin, 2012; Chapter 5, pp 139–183.

Contribution Articles and Others 1. “PROFILE: Early Excellence in Physical Organic Chemistry”

Takeda, Y. J. Phys. Org. Chem. 2016, 29, 116–117. [DOI: 10.1002/poc.3528] https://doi.org/10.1002/poc.3528

2. “有機機能性材料を指向した新規リン含有π共役分子の創製” 武田洋平 生産と技術 技術解説 平成 28 年 新春号（68 巻 1 号）pp27–30. http://seisan.server-shared.com/681/681-27.pdf

3. “ハロゲン結合，結晶工学からの脱却〜有機合成的展開を求めて” 武田洋平，南方聖司 月刊化学 2013, 68(8), 68–69.

4. “MIT 化学科 Swager 研究室での研究生活” 武田洋平 Organometallic News, 2013, 38–39.

5. “マルコフニコフ則を覆す？！〜逐次的触媒反応によるアルケンの位置選択的水和反応〜” Takeda, Y. Kagaku 2012, 67(1), 65.

6. “Cheap Precursor for Arynes” Swager, T. M.; Takeda, Y. Synfacts 2011, 154. [DOI: 10.1055/s-0030-1259251] https://doi.org/10.1055/s-0030-1259251

7. “Perfluorobenzene Captures Fullerene” Swager, T. M.; Takeda, Y. Synfacts 2011, 148. [DOI: 10.1055/s-0030-1259252] https://doi.org/10.1055/s-0030-1259252

19

8. “A New Method for Hypersilyl Aromatic Compounds” Swager, T. M.; Takeda, Y. Synfacts 2011, 34. [DOI: 10.1055/s-0030-1259153] https://doi.org/10.1055/s-0030-1259153

9. “A Versatile Synthetic Method for Silaindenes” Swager, T. M.; Takeda, Y. Synfacts 2011, 31. [DOI: 10.1055/s-0030-1259152] https://doi.org/10.1055/s-0030-1259152

10. “A New Functionalization Method of SWCNTs through Cycloaddition” Swager, T. M.; Takeda, Y. Synfacts 2010, 1361. [DOI: 10.1055/s-0030-1258936] https://doi.org/10.1055/s-0030-1258936

11. “Highly Selective Synthesis of Dibenzo[a,c]cyclooctatetraenes” Swager, T. M.; Takeda, Y. Syntfacts 2010, 1360. [DOI: 10.1055/s-0030-1258937] https://doi.org/10.1055/s-0030-1258937

12. “Swollen-up Molecules by Fragmentation” Swager, T. M.; Takeda, Y. Synfacts 2010, 1246. [DOI: 10.1055/s-0030-1258734] https://doi.org/10.1055/s-0030-1258734

13. “Interplay of Heteroatoms” Swager, T. M.; Takeda, Y. Synfacts 2010, 1241. [DOI: 10.1055/s-0030-1258735] https://doi.org/10.1055/s-0030-1258735

14. “Renaissance of Diels-Alder Reaction of Borylalkenes” Swager, T. M.; Takeda, Y. Synfacts 2010, 1140. [DOI: 10.1055/s-0030-1258629] https://doi.org/10.1055/s-0030-1258629

15. “Break Symmetry, and Get Benefits” Swager, T. M.; Takeda, Y. Synfacts 2010, 1137. [DOI: 10.1055/s-0030-1258640] https://doi.org/10.1055/s-0030-1258640

16. “Low Band Gap Polymers Having Multi-Fused Heterocycles” Swager, T. M.; Takeda, Y. Synfacts 2010, 1010. [DOI: 10.1055/s-0030-1257923] https://doi.org/10.1055/s-0030-1257923

17. “Electrical Stimuli Induced Reversible Self-Assembly” Swager, T. M.; Takeda, Y. Synfacts 2010, 1009. [DOI: 10.1055/s-0030-1257917] https://doi.org/10.1055/s-0030-1257917