Publications


原著論文

原著論文

2021


75.
In(ONf)3-catalyzed 7-membered carbon-ring-forming annulation
of heteroarylindoles with α,β-unsaturated carbonyl compounds

Tsuchimoto, T.; Johshita, T.; Sambai, K.; Saegusa, N.; Hayashi, T.; Tani, T.; Osano, M.
Org. Chem. Front. 2021, 8, 2882–2892.

Note: featured on the front cover picture of issue 12/12 June, 2021.
74.
Stepwise Suzuki–Miyaura Cross‐Coupling of Triborylalkenes Derived from Alkynyl–B(dan)s:
Regioselective and Flexible Synthesis of Tetrasubstituted Alkenes

Tani, T.; Takahashi, N.; Sawatsugawa, Y.; Osano, M.; Tsuchimoto, T.
Adv. Synth. Catal. 2021, 363, 2427–2442.

Note: Invited contribution to the special issue on the subject of “Boron in Catalysis and Organic Synthesis”.
Note: This article also appears in "Hot Topic: C–C Coupling”.

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2020


73.
Zinc/Indium Bimetallic Lewis Acid Relay Catalysis
for Dehydrogenative Silylation/Hydrosilylation Reaction
of Terminal Alkynes with Bis(hydrosilane)s

Tani, T.; Sohma, Y.; Tsuchimoto, T.
Adv. Synth. Catal. 2020, 362, 4098–4108.

Note: featured on the front cover picture of issue 19/September, 2020.
72.
Direct Suzuki–Miyaura Coupling with Naphthalene-1,8-diaminato (dan)-Substituted Organoborons
Yoshida, H.; Seki, M.; Kamio, S.; Tanaka, H.; Izumi, Y.; Li, J.; Osaka, I.; Abe, M.; Andoh, H.;
Yajima, T.; Tani, T.; Tsuchimoto, T. ACS Catal. 2020, 10, 346–351.

Note: selected as one of the most read articles in 12/2019–01/2020.

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2019


71.
A Drastic Effect of TEMPO in Zinc‐Catalyzed Stannylation of Terminal Alkynes with Hydrostannanes via Dehydrogenation and Oxidative Dehydrogenation
Kai, Y.; Oku, S.; Tani, T.; Sakurai, K.; Tsuchimoto, T.
Adv. Synth. Catal. 2019, 361, 4314–4323.

Note: selected as a VIP (very important publication).
70.
Alkylation of Terminal Alkynes under Zinc Lewis Acid Catalysis
and Its Mechanistic Studies

Osano, M.; Kida, T.; Yonekura, K.; Tsuchimoto, T.
Adv. Synth. Catal. 2019, 361, 2825–2831.

Note: selected as a VIP (very important publication).
Note: featured on the inside cover picture of issue 12/June, 2019.
Note: selected as one of the top 10% most downloaded papers in 01/2018–12/2019.

69.
Alkynyl–B(dan)s in Various Palladium-Catalyzed Carbon–Carbon
Bond-Forming Reactions Leading to Internal Alkynes,
1,4-Enynes, Ynones, and Multiply Substituted Alkenes

Tani, T.; Sawatsugawa, Y.; Sano, Y.; Hirataka, Y.; Takahashi, N.; Hashimoto, S.;
Sugiura, T.; Tsuchimoto, T. Adv. Synth. Catal. 2019, 361, 1815–1834.

Note: selected as a VIP (very important publication).
Note: featured on the front cover picture of issue 8/April, 2019.
Note: selected as one of the most accessed articles in 02/2019–01/2020.
Note: selected as one of the top 10% most downloaded papers in 01/2018–12/2019.
Note: selected as one of the most accessed articles in 04/2019–03/2020.

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2018


68.
Indium-Catalyzed Annulation of o-Acylanilines with Alkoxyheteroarenes: Synthesis of Heteroaryl[b]quinolines and Subsequent Transformation to Cryptolepine Derivatives
Yonekura, K.; Shinoda, M.; Yonekura, Y.; Tsuchimoto, T. Molecules 2018, 23, 838.
Note: invited contribution to the special issue on the subject of "Indium in Organic Synthesis".
67.
A Heteroarylamine Library: Indium-Catalyzed Nucleophilic Aromatic Substitution of Alkoxyheteroarenes with Amines
Yonekura, K.; Yoshimura, Y.; Akehi, M.; Tsuchimoto, T. Adv. Synth. Catal. 2018, 360, 1159–1181.
Note: selected as one of the most accessed articles in 02/2018.

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2017


66.
Zinc-Catalyzed Dehydrogenative Silylation of Indoles
Yonekura, K.; Iketani, Y.; Sekine, M.; Tani, T.; Matsui, F.; Kamakura, D.; Tsuchimoto, T. Organometallics 2017, 36, 3234–3249.
65.
Naked d-orbital in a centrochiral Ni(II) complex as a catalyst for asymmetric [3+2] cycloaddition
Sohtome, Y.; Nakamura, G.; Muranaka, A.; Hashizume, D.; Lectard, S.; Tsuchimoto, T.; Uchiyama, M.;
Sodeoka, M. Nat. Commun. 2017, doi: 10.1038/ncomms14875

64.
Indium-Catalyzed Regioselective β-Alkylation of Pyrroles with Carbonyl Compounds and Hydrosilanes and Its Application to Construction of a Quaternary Carbon Center with a β-Pyrrolyl Group
Nomiyama, S.; Ogura, T.; Ishida, H.; Aoki, K.; Tsuchimoto, T. J. Org. Chem. 2017, 82, 5178–5197.

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2016


63.
Indium-Catalyzed Formal N-Arylation and N-Alkylation of Pyrroles with Amines
Yonekura, K.; Oki, K.; Tsuchimoto, T. Adv. Synth. Catal. 2016, 358, 2895–2902.
62.
Carboxylative cyclization of propargylic amines with CO2 catalyzed by dendritic N-heterocyclic carbene–gold(I) complexes
Fujita, K.; Inoue, K.; Sato, J.; Tsuchimoto, T.; Yasuda, H. Tetrahedron 2016, 72, 1205–1212.
61.
Easy Access to a Library of Alkylindoles: Reductive Alkylation of Indoles with Carbonyl Compounds and Hydrosilanes under Indium Catalysis
Nomiyama, S.; Hondo, T.; Tsuchimoto, T. Adv. Synth. Catal. 2016, 358, 1136–1149.

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2015


60.
Alkynylboranes: A Practical Approach by Zinc-Catalyzed Dehydrogenative Coupling of Terminal Alkynes with 1,8-Naphthalenediaminatoborane
Tsuchimoto, T.; Utsugi, H.; Sugiura, T.; Horio, S. Adv. Synth. Catal. 2015, 357, 77–82.
Note: Selected as one of the most accessed articles in 12/2014.

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2014


59.
Metal-Free Regioselective β-Alkylation of Pyrroles with Carbonyl Compounds and Hydrosilanes:
Use of a Brønsted Acid as a Catalyst

Nomiyama, S.; Tsuchimoto, T. Adv. Synth. Catal. 2014, 356, 3881–3891.
58.
Indium-catalyzed heteroaryl–heteroaryl bond formation through nucleophilic aromatic substitution: Preparation of 2-methyl-3-(thien-2-yl)-1H-indole
Nagase, Y.; Tsuchimoto, T. Org. Synth. 2014, 91, 273–282.
57.
Aqueous media carboxylative cyclization of propargylic amines with CO2 catalyzed by amphiphilic dendritic N-heterocyclic carbene–gold(I) complexes
Fujita, K.; Sato, J.; Inoue, K.; Tsuchimoto, T.; Yasuda, H. Tetrahedron Lett. 2014, 55, 3013–3016.
56.
RE12 derivatives displaying Vaccinia H1-related phosphatase (VHR) inhibition in the presence of detergent and their anti-proliferative activity against HeLa cells
Thuaud, F.; Kojima, S.; Hirai, G.; Oonuma, K.; Tsuchiya, A.; Uchida, T.; Tsuchimoto, T.; Sodeoka, M. Bioorg. Med. Chem. 2014, 22, 2771–2782.
55.
Zinc-Catalyzed Direct Cyanation of Indoles and Pyrroles: Nitromethane as a Source of a Cyano Group
Nagase, Y.; Sugiyama, T.; Nomiyama, S.; Yonekura, K; Tsuchimoto, T. Adv. Synth. Catal. 2014, 356, 347–352.

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2013


54.
Indium-Catalyzed Annulation of Indoles with (2-Ethynylaryl)methyl Ethyl Carbonates: Synthesis and Photoluminescent Properties of Aryl- and Heteroaryl[b]carbazoles
Nagase, Y.; Miyamura, T.; Inoue, K.; Tsuchimoto, T. Chem. Lett. 2013, 42, 1170–­1172.
53.
Indium-catalyzed annulation of 3-aryl- and 3-heteroarylindoles with propargyl ethers: synthesis and photoluminescent properties of aryl- and heteroaryl[c]carbazoles
Nagase, Y.; Shirai, H.; Kaneko, M.; Shirakawa, E.; Tsuchimoto, T. Org. Biomol. Chem. 2013, 11, 1456–­1459.

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2012


52.
Homogeneous Dihydroxylation of Olefins Catalyzed by OsO42- Immobilized on a Dendritic Backbone with a Tertiary Nitrogen at Its Core Position
Fujita, K.; Inoue, K.; Tsuchimoto, T.; Yasuda, H. Chem. Pharm. Bull. 2012, 60(12), 1594–­1598.
51.
Dehydrogenative Silylation of Terminal Alkynes with Hydrosilanes under Zinc-Pyridine Catalysis
Tsuchimoto, T.; Fujii, M.; Iketani, Y.; Sekine, M. Adv. Synth. Catal. 2012, 354, 2959–­2964.
Note: Selected as one of the most accessed articles in 10/2012.
50.
Zinc-Catalyzed Dehydrogenative N-Silylation of Indoles with Hydrosilanes
Tsuchimoto, T.; Iketani, Y.; Sekine, M. Chem. Eur. J. 2012, 18, 9500–­9504.

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2011


49.
Development of new catalytic reactions based on activation of hydrocarbon functional groups by Lewis acids
Tsuchimoto, T. J. Synth. Org. Chem., Jpn. 2011, 69, 889–903.
Note: invited, as an account for Incentive Award in Synthetic Organic Chemistry, Japan (2009).
48.
Catalytic asymmetric α-chlorination of 3-acyloxazolidin-2-one with a trinary catalytic system
Hamashima, Y.; Nagi, T.; Shimizu, R.; Tsuchimoto, T.; Sodeoka, M. Eur. J. Org. Chem. 2011, 3675–3678.
Note: Highlighted in Synfacts 2011, 993.
47.
Magnetically recoverable osmium catalysts for dihydroxylation of olefins
Fujita, K.; Umeki, S.; Yamazaki, M.; Ainoya, T.; Tsuchimoto, T.; Yasuda, H. Tetrahedron Lett. 2011, 52, 3137–3140.
Note: Highlighted in Synfacts 2011, 916.
46.
Reductive alkylation of indoles with alkynes and hydrosilanes under indium catalysis
Tsuchimoto, T.; Kanbara, M. Org. Lett. 2011, 13, 912–915.
Note: Highlighted in Synfacts 2011, 535. (Open Access)
45.
Microwave-assisted organic functionalization of silica surfaces: Effect of selectively heating silylating agents
Fukaya, N.; Yamashita, H.; Haga, H.; Tsuchimoto, T.; Onozawa, S.; Sakakura, T.; Yasuda, H. J. Organomet. Chem. 2011, 696, 825–828.
44.
Indium-catalyzed heteroaryl–heteroaryl bond formation through nucleophilic aromatic substitution
Tsuchimoto, T.; Iwabuchi, M.; Nagase, Y.; Oki, K.; Takahashi, H. Angew. Chem. Int. Ed. 2011, 50, 1375–1379.
43.
Selective synthesis of β-alkylpyrroles
Tsuchimoto, T. Chem. Eur. J. 2011, 17, 4064–4075.
Note: invited, as Concepts article.
Note: Selected as one of the most accessed articles in 3/2011.

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2010


42.
A recyclable dendritic osmium catalyst for homogeneous dihydroxylation of olefins
Fujita, K.; Yamazaki, M.; Ainoya, T.; Tsuchimoto, T.; Yasuda, H. Tetrahedron 2010, 66, 8536–8543.
Note: Highlighted in Synfacts 2011, 110.
41.
Organic functionalization of the surface of silica with arylsilanes. A new method for synthesizing organic–inorganic hybrid materials
Fukaya, N.; Haga, H.; Tsuchimoto, T.; Onozawa, S.; Sakakura, T.; Yasuda, H. J. Organomet. Chem. 2010, 695, 2540–2542.
40.
Exclusive synthesis of β-alkylpyrroles under indium catalysis: carbonyl compounds as sources of alkyl groups
Tsuchimoto, T.; Igarashi, M.; Aoki, K. Chem. Eur. J. 2010, 16, 8975–8979.
Note: Highlighted in Synfacts 2010, 1138.
39.
Homogeneous dihydroxylation of olefins catalyzed by a recyclable OsO42- core dendrimer
Fujita, K.; Ainoya, T.; Tsuchimoto, T.; Yasuda, H. Tetrahedron Lett. 2010, 51, 808–810.
Note: Highlighted in Synfacts 2010, 495.

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2009


38.
Indium-catalyzed reductive alkylation of pyrroles with alkynes and hydrosilanes: selective synthesis of β-alkylpyrroles.
Tsuchimoto, T.; Wagatsuma, T.; Aoki, K.; Shimotori, J. Org. Lett. 2009, 11, 2129–2132.
Note: Highlighted as Noteworthy Chemistry in ACS home page.
37.
Synthesis of methanes having four different carbon substituents utilizing indium-catalyzed cleavage of carbon–pyrrolyl bonds
Tsuchimoto, T.; Ainoya, T.; Aoki, K.; Wagatsuma, T.; Shirakawa, E. Eur. J. Org. Chem. 2009, 2437–2440.

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2008


36.
Indium-catalyzed annulation of 2-aryl- and 2-heteroarylindoles with propargyl ethers: concise synthesis and photophysical properties of diverse aryl- and heteroaryl-annulated[a]carbazoles.
Tsuchimoto, T.; Matsubayashi, H.; Kaneko, M.; Nagase, Y.; Miyamura, T.; Shirakawa, E. J. Am. Chem. Soc. 2008, 130, 15823–15835.
35.
Lewis acid-catalyzed addition of pyrazoles to alkynes: selective synthesis of double and single addition products.
Tsuchimoto, T.; Aoki, K.; Wagatsuma, T.; Suzuki, Y. Eur. J. Org. Chem. 2008, 4035–4040.

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2007


34.
Stereochemistry in Lewis acid-catalyzed silylation of alcohols, silanols, and methoxy- silanes with optilcally active methyl(1-naphthyl)phenylsilane
Shinke, S.; Tsuchimoto, T.; Kawakami, Y. Silicon Chem. 2007, 3, 243–249.

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2006


33.
Ruthenium-catalyzed addition of terminal alkynes to alkynylstannanes with migration of the stannyl group
Shirakawa, E.; Nakayama, K.; Morita, R.; Tsuchimoto, T.; Kawakami, Y. Bull. Chem. Soc. Jpn. 2006, 79, 1963–1976.
32.
Studies on Carbon–Carbon Bond Forming Reactions Utilizing Activation of Unsaturated Hydrocarbons and Heteroaromatic Compounds by Metal Sulfonate Catalysts
Tsuchimoto, T. J. Synth. Org. Chem., Jpn. 2006, 64, 752–765.
Note: invited, as an account.
31.
Nickel-catalyzed addition of organoboronates to 1,2-dienes and the corresponding three-component reaction with an alkyne.
Takahashi, G.; Shirakawa, E.; Tsuchimoto, T.; Kawakami, Y. Adv. Synth. Catal. 2006, 348, 837–840.

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2005


30.
A simple catalyst system for the palladium-catalyzed coupling of aryl halides with terminal alkynes
Shirakawa, E.; Kitabata, T.; Otsuka, H.; Tsuchimoto, T. Tetrahedron 2005, 61, 9878–9885.
29.
Synthesis of multisubstituted 1,3-butadienes using the ruthenium-catalyzed double addition of trimethylsilyldiazomethane to alkynylboronates
Morita, R.; Shirakawa, E.; Tsuchimoto, T.; Kawakami, Y. Org. Biomol. Chem. 2005, 3, 1263–1268.
28.
Alkynes as activators in the nickel-catalyzed addition of organoboronates to aldehydes
Takahashi, G.; Shirakawa, E.; Tsuchimoto, T.; Kawakami, Y. Chem. Commun. 2005, 1459–1461.
27.
Easy access to aryl- and heteroaryl-annulated[a]carbazoles by indium-catalyzed reaction of 2-arylindoles with propargyl ethers
Tsuchimoto, T.; Matsubayashi, H.; Kaneko, M.; Shirakawa, E.; Kawakami, Y. Angew. Chem. Int. Ed. 2005, 44, 1336–1340.

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2004


26.
Synthetic strategy for functionalized polyacene structure using nickel-catalyzed alkynylstannylation of 1,2-dienes
Nakao, Y.; Tsuchimoto, T.; Shirakawa, E.; Hiyama, T. Trans. MRS-J. 2004, 29, 93–96.
25.
Ruthenium-catalyzed hydrogenation of alkynylstannanes with migration of the stannyl group
Shirakawa, E.; Morita, R.; Tsuchimoto, T.; Kawakami, Y. J. Am. Chem. Soc. 2004, 126, 13614–13615.
24.
A p-phosphinophenolate ligand for the palladium-catalyzed arylation of alkenes
Shirakawa, E.; Ishii, K.; Tsuchimoto, T. Chem. Commun. 2004, 2752–2753.
23.
Nickel-catalyzed acylstannylation and alkynylstannylation of 1,2-dienes
Nakao, Y.; Shirakawa, E.; Tsuchimoto, T.; Hiyama, T. J. Organomet. Chem. 2004, 689, 3701–3721.
22.
Zirconium triflate catalyzed direct coupling reaction of lactams with heterocyclic arenes under atmospheric oxygen
Tsuchimoto, T.; Ozawa, Y.; Negoro, R.; Shirakawa, E.; Kawakami, Y. Angew. Chem. Int. Ed. 2004, 43, 4231–4233.
Note: Selected as a Hot paper.
21.
Nickel-catalyzed tandem carbostannylation of alkynes and 1,2-dienes with alkynyl-stannanes
Shirakawa, E.; Yamamoto, Y.; Nakao, Y.; Oda, S.; Tsuchimoto, T.; Hiyama, T. Angew. Chem. Int. Ed. 2004, 43, 3448–3451.

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2003


20.
Indium triflate-catalyzed double addition of heterocyclic arenes to alkynes
Tsuchimoto, T.; Hatanaka K.; Shirakawa, E.; Kawakami, Y. Chem. Commun. 2003, 2454–2455.
19.
Palladium-catalyzed dimerization of vinylarenes using indium triflate as an effective co-catalyst
Tsuchimoto, T.; Kamiyama, S.; Negoro, R.; Shirakawa, E.; Kawakami, Y. Chem. Commun. 2003, 852–853.

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2002


18.
Nickel-catalyzed addition of organoboronates to 1,3-dienes
Shirakawa, E.; Takahashi, G.; Tsuchimoto, T.; Kawakami, Y. Chem. Commun. 2002, 2210–2211.
17.
Synthesis of polycyclic compounds utilizing the nickel-catalyzed alkynylstannylation of 1,2-dienes
Shirakawa, E.; Nakao, Y.; Tsuchimoto, T.; Hiyama, T. Chem. Commun. 2002, 1962–1963.

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2001


16.
Nickel-catalyzed hydroarylation of alkynes using arylboron compounds: selective synthesis of multisubstituted arylalkenes and aryldienes
Shirakawa, E.; Takahashi, G.; Tsuchimoto, T.; Kawakami, Y. Chem. Commun. 2001, 2688–2689.
15.
Transition metal-catalyzed acylation of α,β-unsaturated carbonyl compounds with acylstannanes
Shirakawa, E.; Yamamoto, Y.; Nakao, Y.; Tsuchimoto, T.; Hiyama, T. Chem. Commun. 2001, 1926-1927.

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2000


14.
Friedel–Crafts alkenylation of arenes using alkynes catalyzed by metal trifluoromethane-sulfonates
Tsuchimoto, T.; Maeda, T.; Shirakawa, E.; Kawakami, Y. Chem. Commun. 2000, 1573–1574.
13.
Brønsted acid-catalyzed hydration of alkynes: a convenient route to diverse carbonyl compounds
Tsuchimoto, T.; Joya, T.; Shirakawa, E.; Kawakami, Y. Synlett 2000, 1777–1778.

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1999


12.
Synthetic applications of ortho esters
Wipf, P.; Tsuchimoto, T.; Takahashi, H. Pure Appl. Chem. 1999, 71, 415–422.

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1997


11.
Superacid-catalyzed reductive Friedel–Crafts reaction of arenes using arenecarbaldehyde acetals
Fukuzawa, S.; Tsuchimoto, T.; Hiyama, T. J. Org. Chem. 1997, 62, 151–156.
10.
Scandium(III) triflate-catalyzed Friedel–Crafts alkylation reactions
Tsuchimoto, T.; Tobita, K.; Hiyama, T.; Fukuzawa, S. J. Org. Chem. 1997, 62, 6997–7005.

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1996


9.
Scandium(III) triflate catalyzed Friedel–Crafts alkylation with benzyl and allyl alcohols
Tsuchimoto, T.; Tobita, K.; Hiyama, T.; Fukuzawa, S. Synlett 1996, 557–559.
8.
Scandium(III) trifluoromethanesulfonate-catalyzed reductive Friedel–Crafts benzylation of aromatic compounds using arenecarbaldehydes and propane-1,3-diol
Tsuchimoto, T.; Hiyama, T.; Fukuzawa, S. Chem. Commun. 1996, 2345–2346.
7.
Samarium(II) triflate as a new reagent for the Grignard-type carbonyl addition reaction
Fukuzawa, S.; Mutoh, K.; Tsuchimoto, T.; Hiyama, T. J. Org. Chem. 1996, 61, 5400–5405.
6.
Alkylation–annulation of halo esters with organometallic reagent/SmI2 couple leading to cycloalkanols: a facile cyclopropanol synthesis from a halo ester
Fukuzawa, S.; Furuya, H.; Tsuchimoto, T. Tetrahedron 1996, 52, 1953–1960.

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1995


5.
Direct synthesis of chiral acetals from carbonyl compounds and chiral diols: sequential one-pot asymmetric silylcyanation reaction catalyzed by scandium(III) triflate
Fukuzawa, S.; Tsuchimoto, T.; Hotaka, T.; Hiyama, T. Synlett 1995, 1077–1078.
4.
A facile conversion of substituted cyclobutanones to cyclopentanones by CH2I2/SmI2 system
Fukuzawa, S.; Tsuchimoto, T. Tetrahedron Lett. 1995, 36, 5937–5938.

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1994


3.
Preparation of samarium(II) triflate and it mediated Grignard-type reaction.  In situ formation and reaction of new organosamarium reagents 
Fukuzawa, S.; Tsuchimoto, T.; Kanai, T. Chem. Lett. 1994, 1981–1984.
2.
Ytterbium trifluoromethanesulfonate mediated cross-aldol reaction between ketones and aldehydes
Fukuzawa, S.; Tsuchimoto, T.; Kanai, T. Bull. Chem. Soc. Jpn. 1994, 67, 2227–2232.

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1993


1.
Samarium(II) diiodide induced intramolecular coupling reaction of haloacetals leading to the synthesis of γ-lactones
Fukuzawa, S.; Tsuchimoto, T. Synlett 1993, 803–804.

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著書 (books)


1.
有機合成化学協会編, " 2 版有機合成実験法ハンドブック", 丸善出版, 共著 (2015) .
総ページ数 : 1166, 担当章 : 19.3.12 インジウム, 担当頁 : pp. 654–658, 2015 11 30 日発行

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記事・解説


4.
N–H 結合と H–C 結合の直接カップリング
土本晃久, Organometallic News, 2008, 82.
3.
オリゴチオフェン
土本晃久, 有合化, 2006, 64, 782.
2.
光学活性アミンを不斉源とする華麗な触媒的不斉合成反応
土本晃久, 化学と工業, 2001, 54, 1392.
1.
Pd 触媒による C–N ヘテロクロスカップリング反応の機構
福沢信一, 土本晃久, Organometallic News, 1994, 125.

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