Kohei Fuchibe Publication List April 23, 2016

D 3461

Angewandte C

hemie International Edition 2009, N

umber 43, Pages 7941–8150

www.angewandte.org

ACIEFS 48 (43) 7941–8150 (2009) · ISSN 1433–7851 · Vol. 48 · No. 43

2009–48/43

Poly(2-oxazoline)s R. Hoogenboom1,3-Dipolar Cycloaddition B. Engels and M. ChristlStereoselective Aldol Synthesis D. B. Werz and D. C. KoesterC–F Bond Activation T. G. Driver

Cover Picture, publication # 44

Cover Picture, publication # 57

1) N. Iwasawa, K. Fuchibe, ‘Synthesis of α-Methoxy-α,β-Unsaturated Esters by Iodine-oxidation of the Anions of Fischer-type Carbene Complexes,’ Chem. Lett. 1998, 1149–1150.

2) K. Fuchibe, N. Iwasawa, ‘A Novel Use of the Anions of Fischer-type Carbene Complexes as Alkenyl Metallic Species,’ Tetrahedron 2000, 56, 4907–4915.

3) K. Fuchibe, N. Iwasawa, ‘Reactions of Novel Reactive Species Generated by Samarium(II)-mediated One-electron Reduction of Fischer-type Carbene Complexes,’ Org. Lett. 2000, 2, 3297–3299.

4) T. Akiyama, J. Itoh, K. Fuchibe, ‘Mannich-type Reaction Catalyzed by HBF4 in Water: Effect of the Loading of Surfactant,’ Synlett 2002, 1269–1272.

5) K. Sangu, H. Kagoshima, K. Fuchibe, T. Akiyama, ‘Novel Thermal Reaction of Fischer Carbene Complexes with Imines: Synthesis of β-Methoxy Allylic Amine Derivatives,’ Org. Lett. 2002, 4, 3967–3969.

6) T. Akiyama, K. Matsuda, K. Fuchibe, ‘Montmorillonite K10-catalyzed Aza-Diels-Alder Reaction of Danishefsky's Diene with Aldimines, Generated in situ from Aliphatic Aand an Amine, in Aqueous Media,’ Synlett 2002, 1898–1900.

7) K. Fuchibe, N. Iwasawa, ’Generation of Reactive Species by One-electron Reduction of Fischer-type Carbene Complexes of Group 6 Metals and Their Use for Carbon-carbon Bond Formation,’ Chem. Eur. J. 2003, 9, 905–914.

8) T. Akiyama, S. Ogi, K. Fuchibe, ‘Stereoselective Synthesis of CF3-substituted Aziridines by Lewis Acid-mediated Aziridination of Aldimines with Diazoacetates,’ Tetrahedron Lett. 2003, 44, 4011–4013.

9) T. Akiyama, M. Hara, K. Fuchibe, S. Sakamoto, K. Yamaguchi, ‘Synthesis of a Novel Crown Ether Derived from Chiro-inositol and Its Catalytic Activity on the Asymmetric Michael Addition,’ Chem. Commun. 2003, 1734–1735.

10) T. Akiyama, M. Sanada, K. Fuchibe, ‘Brønsted Acid-mediated Synthesis of α-Amino Phosphonates under Solvent-free Conditions’, Synlett 2003, 1463–1464.

11) T. Akiyama, K. Daidouji, K. Fuchibe, ‘Cu(I)-Catalyzed Enantioselective [2 + 2] Cycloaddition of 1-Methoxyallenylsilane with α-Imino Ester: Chiral Synthesis of α,β-Unsaturated Acylsilanes,’ Org. Lett. 2003, 5, 3691–3693.

12) K. Sangu, K. Fuchibe, T. Akiyama, ‘A Novel Approach to 2-Arylated Quinolines: Electrocyclization of Alkynyl Imines via Vinylidene Complexes,’ Org. Lett. 2004, 6, 353–355.

13) T. Akiyama, S. Nakashima, K. Yokota, K. Fuchibe, ‘Synthesis of Aryl-substituted Quinoline Derivatives via Bronsted Acid-Catalyzed [4+2] Aza Diels-Alder Reaction,’ Chem. Lett. 2004, 33, 922–923.

14) T. Akiyama, J. Itoh, K. Yokota, K. Fuchibe, ‘Enantioselective Mannich-type Reaction Catalyzed by a Chiral Brønsted Acid,’ Angew. Chem. Int. Ed. 2004, 43, 1566–1568.

15) K. Fuchibe, T. Akiyama, ‘Niobium-catalyzed Reduction of Monofluoroarenes with LiAlH4,’ Synlett 2004, 1282–1284.

16) K. Fuchibe, Yuji Aoki, T. Akiyama, ‘[3+2] Cycloaddition Reactions of Cyclopropylmethylsilanes and α-Keto Aldehydes: Trans- and Cis-selective Formation of 2-Silylmethyltetrahydrofurans,’ Chem. Lett. 2005, 34, 538–539.

17) T. Akiyama, K. Matsuda, K. Fuchibe, ‘Montmorillonite K10-Catalyzed Nucleophilic Addition Reaction to Aldimines in Water (Special Topic: Aqueous Chemistry: Invited),’ Synthesis, 2005, 2606–2608.

18) T. Akiyama, H. Morita, J. Itoh, K. Fuchibe, ‘Chiral Brønsted Acid-catalyzed Enantioselective Hydrophosphonylation of Imines: Asymmetric Synthesis of α-Amino Phosphonates,’ Org. Lett. 2005, 7, 2583–2585.

19) T. Akiyama, A. Suzuki, K. Fuchibe, ‘Mannich-type Reaction Promoted by an Ionic Liquid,’ Synlett, 2005, 1024–1026.

20) K. Daidouji, K. Fuchibe, T. Akiyama, ‘Cu(I)-Catalyzed Enantioselective [3+2] Cycloaddition Reaction of 1-Alkylallenylsilanewith α-Imino Ester: Chiral Synthesis of Pyrroline Derivatives,’ Org. Lett. 2005, 7, 1051–1053.

21) T. Akiyama, K. Matsuda, K. Fuchibe, ‘HCl-catalyzed Stereoselective Mannich Reaction in H2O-SDS System’, Synlett, 2005, 322–324.

22) T. Akiyama, Y. Saitoh, H. Morita, K. Fuchibe, ‘Enantioselective Mannich-type Reaction Catalyzed by a Brønsted Acid Derived from TADDOL,’ Adv. Synth. Catal. 2005, 347, 1523–1526.

23) K. Fuchibe, R. Hatemata, T. Akiyama, ‘Enantioselective Three-Component Synthesis of 4-Arylated Dehydroprolines: [3+2] Annulation of Allenylstannane and α-Imino Ester,’ Tetrahedron Lett. 2005, 46, 8563–8566.

24) T. Akiyama, K. Fuchibe, J. Itoh, ‘Brønsted Acid-Catalyzed Addition and Cyclization Reaction with Imine: From Aqueous Reaction to Enantioselective Reactions,’ J. Synth. Org. Chem., Jpn., 2005, 63, 1062–1068.

25) T. Akiyama, S. Funaki, K. Fuchibe, ‘Stereoselective Synthesis of Tetrahydrofuran by Diastereoselective [3+2] Cycloaddition Reaction of Chiral Allylsilane with α-Keto Ester,’ Heterocycles, 2006, 369–374.

26) K. Fuchibe, T. Akiyama, ‘Low-Valent Niobium-Mediated Double Activation of C–F/C–H Bonds: Fluorene Synthesis from o-Arylated α,α,α-Trifluorotoluene Derivatives,’ J. Am. Chem. Soc. 2006, 128, 1434–1435.

27) T. Akiyama, T. Tamura, J. Itoh, H. Morita, K. Fuchibe, ‘Enantioselective Aza-Diels-Alder Reaction Catalyzed by a Chiral Brønsted Acid: Effect of the Additive on the Enantioselectivity,’ Synlett 2006, 141–143.

28) K. Fuchibe, D. Ono, T. Akiyama, ‘Synthesis of Pyrroles: Reaction of Chromium N-Alkylaminocarbene Complexes with α,β-Unsaturated Aldehydes,’ Chem. Commun. 2006, 2271–2273.

29) T. Akiyama, H. Morita, K. Fuchibe, ‘Chiral Brønsted Acid-Catalyzed Inverse Electron-Demand Aza Diels-Alder Reaction,’ J. Am. Chem. Soc. 2006, 128, 13070–13071.

30) J. Itoh, K. Fuchibe, T. Akiyama, ‘Chiral Brønsted Acid-Catalyzed Enantioselective Aza-Diels-Alder Reaction of Brassard’s Diene with Imines,’ Angew. Chem. Int. Ed. 2006, 45, 4796–4798.

31) K. Fuchibe, R. Hatemata, T. Akiyama, ‘One-Pot Synthesis of Chiral Dehydroproline Esters: [3+2]-Type Cycloaddition Reaction of Allenylstannane and α-Imino Ester,’ Tetrahedron 2006, 62,11304– 11310.

32) J. Itoh, K. Fuchibe, T. Akiyama, ‘Mannich-type Reaction in Water in the Presence of a Surfactant,’ Synthesis 2006, 4075–4080.

33) T. Akiyama, J. Itoh, K. Fuchibe, ‘Recent Progress in Chiral Brønsted Acid Catalysis,’ Adv. Synth. Catal. 2006, 348, 999–1010.

34) K. Fuchibe, K. Mitomi, T. Akiyama, ‘Low-valent Niobium-mediated Synthesis of Indenes: Intramolecular Coupling Reaction of CF3 Group with Alkene C–H Bond,’ Chem. Lett. 2007, 36, 24–25.

35) H. Kagoshima, K. Fuchibe, T. Akiyama, ‘Synthesis of Nitrogen-containing Compounds Using Chromium Fischer Carbene Complexes,’ Chem. Rec. 2007, 7, 104–114.

36) K. Fuchibe, Y. Ohshima, K. Mitomi, T. Akiyama, ‘Low-Valent Niobium-Catalyzed Reduction of α,α,α-Trifluorotoluenes,’ Org. Lett. 2007, 9, 1497-1499.

37) M. Yamanaka, J. Itoh, K. Fuchibe, T. Akiyama, ‘Chiral Brønsted Acid Catalyzed Enantioselective Mannich-Type Reaction,’ J. Am. Chem. Soc. 2007, 129, 6756–6764.

38) K. Fuchibe, Y. Ohshima, K. Mitomi, T. Akiyama,’Hydrodefluorinations by Low-valent Niobium Catalyst,’ J. Fluorine Chem. 2007, 128, 1158–1167.

39) T. Akiyama, Y. Honma, J. Itoh, K. Fuchibe, ‘Vinylogous Mannich-type Reaction Catalyzed by an Iodine-substituted Chiral Phosphoric Acid,’ Adv. Synth. Catal. 2008, 350, 399–402.

40) K. Fuchibe, K. Mitomi, R. Suzuki, T. Akiyama, ‘C–C coupling Reactions of Superstrong CF3 Groups with C(sp2)–H Bonds: Reactivity and Synthetic Utility of Zero-valent Niobium Catalyst,’ Chem. Asian J. 2008, 3, 261–271.

41) J. Itoh, K. Fuchibe, T. Akiyama, ‘Preparation of β-Amino Esters by a Chiral Brønsted Acid-catalyzed Mannich-type Reaction,’ Synthesis 2008, 1319–1322.

42) J. Itoh, K. Fuchibe, T. Akiyama, ‘Chiral Phosphoric Acid Catalyzed Enantioselective Friedel-Crafts Alkylation of Indoles with Nitroalkenes: Cooperative Effect of 3A Molecular Sieves,’ Angew. Chem. Int. Ed. 2008, 47, 4016–4018.

43) K. Fuchibe, T. Akiyama, ‘Catalytic Activation of Carbon-fluorine Bonds by Low-valent Niobium Species,’ J. Synth. Org. Chem., Jpn. 2009, 67, 208–218.

44) K. Fuchibe, T. Kaneko, K. Mori, T. Akiyama, ‘Expedient Synthesis of N-Fused Indoles: A C–F Activation and C–H Insertion Approach,’ Angew. Chem. Int. Ed. 2009, 48, 8070–8073 (Selected to the Cover Picture).

Highlight Article: T. G. Driver, ‘Niobium-Catalyzed Activation of Aryl Trifluoromethyl Groups and Functionalization of C–H Bonds: an Efficient and Convergent Approach to the Synthesis of N-Heterocycles,’ Angew. Chem. Int. Ed. 2009, 48, 7974–7976.

C & E News: ‘Double C–F/C–H Bond Activation,’ 2006, 36 (issue of Jan. 30).

45) M. Yokota, K. Fuchibe, M. Ueda, Y. Mayumi, J. Ichikawa, ‘Facile Synthesis of 1,1-Difluoroallenes via the Difluorovinylidenation of Aldehydes and Ketones,’ Org. Lett. 2009, 11, 3994–3997.

46) R. Nadano, K. Fuchibe, M. Ikeda, H. Takahashi, J. Ichikawa, ‘Rapid and Slow Generation of 1-Trifluoromethylvinyllithium: Syntheses and Applications of CF3-Containing Allylic Alcohols, Allylic Amines, and Vinyl Ketones,’ Chem. Asian J. 2010, 5, 1875–1883.

47) K. Fuchibe, K. Atobe, Y. Fujita, K. Mori, T. Akiyama ‘Niobium-catalyzed Activation of CF3 Group on Alkene: Synthesis of Substituted Indenes,’ Chem. Lett. 2010, 39, 867–869.

48) K. Oh, K. Fuchibe, J. Ichikawa, ‘Synthesis of 1,1-Difluoroallenes from Commercially Available 1,1,1-Trifluoro-2-iodoethane,’ Synthesis 2011, 881–886.

49) K. Fuchibe, H. Jyono, M. Fujiwara, T. Kudo, M. Yokota, J. Ichikawa, ‘Domino Friedel–Crafts-Type Cyclizations of Difluoroalkenes Utilizing the α-Cation-Stabilizing Effect of Fluorine: An Efficient Method for Synthesizing Angular PAHs,’ Chem. Eur. J. 2011, 17, 12175–12185.

50) K. Fuchibe, Y. Koseki, H. Sasagawa, J. Ichikawa, ‘NHC-Catalyzed Difluorocarbene Generation and its Application to Aryl Difluoromethyl Ether Synthesis,’ Chem. Lett. 2011, 40, 1189–1191.

51) T. Fujita, T. Ichitsuka, K. Fuchibe, J. Ichikawa, ‘Facile Synthesis of β,β-Difluorostyrenes via the Negishi Coupling of Thermally Stable 2,2-Difluorovinyl Zinc-TMEDA Complex,’ Chem. Lett. 2011, 40, 986–988.

52) K. Fuchibe, Y. Koseki, T. Aono, H. Sasagawa, J. Ichikawa, ‘NHC-Catalyzed Generation of Difluorocarbene and its Application to Difluoromethylation of Oxygen Nucleophiles,’ J. Fluorine Chem. 2012, 133, 52–60.

53) K. Oh, K. Fuchibe, M. Yokota, J. Ichikawa, ‘Facile Synthesis of Substituted 1,1-Difluoroallenes via Carbonyl Difluorovinylidenation,’ Synthesis 2012, 44, 857–861.

54) K. Fuchibe, M. Ueda, M. Yokota, J. Ichikawa, ‘γ-Selective Addition to 1,1-Difluoroallenes: Three-Component Coupling Leading to 2,2-Disubstituted 1,1-Difluoroalkenes,’ Chem. Lett. 2012, 41, 1619–1621.

55) K. Fuchibe, M. Takahashi, J. Ichikawa, ‘Substitutions of Two Fluorines in a Trifluoromethyl Group: Regioselective Synthesis of 3-Fluoropyrazoles,"’Angew. Chem. Int. Ed. 2012, 51, 12059–12062.

56) K. Fuchibe, Y. Mayumi, N. Zhao, S. Watanabe, M. Yokota, J. Ichikawa, ‘Domino Synthesis of Fluorine-Substituted PAHs: 1,1-Difluoroallenes as Synthetic Platforms,’ Angew. Chem. Int. Ed., 2013, 52, 7825–7828.

(‘Polycyclic Aromatic Hydrocarbons from 1,1-Difluoroallenes,’Synfacts 2013, 9, 1060–1060.)

57) K. Fuchibe, Y. Mayumi, M. Yokota, H, Aihara, J. Ichikawa, ‘Indium(III)-Catalyzed Cationic Cyclization of 1,1-Difluoroallenes: Regioselective Synthesis of 1-Fluoronaphthalenes,’ Bull. Chem. Soc. Jpn. 2014, 87, 942–949 (Selected to the Cover Picture).

(BCSJ Award Article, 2014, issue 9) 58) K. Fuchibe, M. Bando, R. Takayama, J. Ichikawa, ‘Organocatalytic, Difluorocarbene-Based

S-Difluoromethylation of Thiocarbonyl Compounds,’ J. Fluorine Chem. 2015, 171, 133–138.

59) K. Fuchibe, T. Morikawa, K. Shigeno, T. Fujita, J. Ichikawa, ‘ Pinpoint-Fluorinated Phenacenes: New Synthesis and Solubility Enhancement Strategies,’ Org. Lett. 2015, 17,1126–1129.

60) K. Fuchibe, T. Morikawa, R. Ueda, T. Okauchi, J. Ichikawa, ‘Pinpoint-Fluorinated Phenanthrene Synthesis Based on C–F Bond Activation of Difluoroalkenes,’ J. Fluorine Chem. 2015, 179, 106–115.

61) T. Aono, H. Sasagawa, K. Fuchibe, J. Ichikawa, ‘Regioselective Synthesis of α, α-Difluorocyclopentanone Derivatives: Domino Nickel-Catalyzed Difluorocyclopropanation/Ring Expansion Sequence of Silyl Dienol Ethers,’ Org. Lett. 2015, 17, 5736–5739.