Seijiro Matsubara

Summary

Affiliation: Kyoto University
Country: Japan

Publications

  1. ncbi request reprint Palladium-catalyzed decarboxylation and decarbonylation under hydrothermal conditions: decarboxylative deuteration
    Seijiro Matsubara
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoudai katsura, Nishikyo, Kyoto 615 8510, Japan
    Org Lett 6:2071-3. 2004
  2. doi request reprint Reaction pathway of methylenation of carbonyl compounds with bis(iodozincio)methane
    Mutsumi Sada
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoudai katsura, Nishikyo, Kyoto 615 8510, Japan
    J Am Chem Soc 132:17452-8. 2010
  3. doi request reprint Asymmetric synthesis of 1,3-dioxolanes by organocatalytic formal [3 + 2] cycloaddition via hemiacetal intermediates
    Keisuke Asano
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigaku katsura, Nishikyo, Kyoto 615 8510, Japan
    Org Lett 14:1620-3. 2012
  4. doi request reprint Nickel-catalyzed cycloaddition of vinylcyclopropanes to imines
    Rihoko Tombe
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615 8510, Japan
    Org Lett 15:1791-3. 2013
  5. doi request reprint Synthesis of quinolones by nickel-catalyzed cycloaddition via elimination of nitrile
    Kenichiro Nakai
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615 8510, Japan
    Org Lett 15:856-9. 2013
  6. doi request reprint Organocatalytic asymmetric oxy-Michael addition to a γ-hydroxy-α,β-unsaturated thioester via hemiacetal intermediates
    Takaaki Okamura
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigaku katsura, Nishikyo, Kyoto 615 8510, Japan
    Chem Commun (Camb) 48:5076-8. 2012
  7. doi request reprint Nickel-catalyzed cycloaddition of salicylic acid ketals to alkynes via elimination of ketones
    Akihiro Ooguri
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615 8510, Japan
    J Am Chem Soc 131:13194-5. 2009
  8. doi request reprint Silver-catalyzed intramolecular chloroamination of allenes: easy access to functionalized 3-pyrroline and pyrrole derivatives
    Masahiro Sai
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto Daigaku Katsura, Nishikyo ku, Kyoto 615 8510, Japan
    Org Lett 13:4676-9. 2011
  9. doi request reprint Nickel-catalyzed [4 + 2] cycloaddition of enones with alkynes
    Ichiro Koyama
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615 8510, Japan
    J Am Chem Soc 131:1350-1. 2009
  10. doi request reprint Nickel-catalyzed cycloaddition of anthranilic acid derivatives to alkynes
    Nobuyoshi Maizuru
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto, Japan
    Org Lett 13:1206-9. 2011

Collaborators

  • Keisuke Asano
  • Masanobu Uchiyama
  • Takuya Kurahashi
  • Kenichi Nomura
  • Mutsumi Sada
  • Tasuku Inami
  • Hiroaki Horie
  • Takuya Ozawa
  • Kenichiro Nakai
  • Koichiro Oshima
  • Kyohei Fujiwara
  • Saori Sako
  • Ichiro Koyama
  • Takaharu Hirayama
  • Rihoko Tombe
  • Yukihiro Fukata
  • Takaaki Okamura
  • Ryota Wakabayashi
  • Masahiro Sai
  • Yosuke Ochi
  • Nobuyoshi Maizuru
  • Yoshiaki Takada
  • Shinsuke Komagawa
  • Yasufumi Yoshino
  • Akihiro Ooguri
  • Masami Kobata
  • Yuichi Kajita
  • Kiitiro Utimoto
  • Hideaki Yoshino
  • Satoshi Horike
  • Zenichi Ikeda
  • Mitsuru Yamamoto
  • Yoko Baba
  • Taniyuki Furuyama
  • Tsuyoshi Mizuno
  • Motohiro Mizuno
  • Narihiro Toda
  • Ryotaro Matsuda
  • Susumu Kitagawa
  • Kazunaka Endo
  • Daisuke Tanaka
  • Katsumi Ukai

Detail Information

Publications43

  1. ncbi request reprint Palladium-catalyzed decarboxylation and decarbonylation under hydrothermal conditions: decarboxylative deuteration
    Seijiro Matsubara
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoudai katsura, Nishikyo, Kyoto 615 8510, Japan
    Org Lett 6:2071-3. 2004
    ..Under the hydrothermal conditions of deuterium oxide, decarbonylative deuteration was observed to give fully deuterated hydrocarbons from carboxylic acids or aldehydes...
  2. doi request reprint Reaction pathway of methylenation of carbonyl compounds with bis(iodozincio)methane
    Mutsumi Sada
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoudai katsura, Nishikyo, Kyoto 615 8510, Japan
    J Am Chem Soc 132:17452-8. 2010
    ..In the second step, the olefination is facilitated by both Zn atoms of the gem-dizinc reagent without an electron transfer process...
  3. doi request reprint Asymmetric synthesis of 1,3-dioxolanes by organocatalytic formal [3 + 2] cycloaddition via hemiacetal intermediates
    Keisuke Asano
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigaku katsura, Nishikyo, Kyoto 615 8510, Japan
    Org Lett 14:1620-3. 2012
    ..The reaction proceeds via the formation of hemiacetal intermediates between γ-hydroxy-α,β-unsaturated ketones and aldehydes...
  4. doi request reprint Nickel-catalyzed cycloaddition of vinylcyclopropanes to imines
    Rihoko Tombe
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615 8510, Japan
    Org Lett 15:1791-3. 2013
    ..A variety of imines can be used in this reaction. An asymmetric variant of the reaction has also been demonstrated...
  5. doi request reprint Synthesis of quinolones by nickel-catalyzed cycloaddition via elimination of nitrile
    Kenichiro Nakai
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615 8510, Japan
    Org Lett 15:856-9. 2013
    ..The reaction involves elimination of a nitrile group by cleavage of the two independent aryl-cyano and aryl-carbonyl C-C bonds of the amides...
  6. doi request reprint Organocatalytic asymmetric oxy-Michael addition to a γ-hydroxy-α,β-unsaturated thioester via hemiacetal intermediates
    Takaaki Okamura
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigaku katsura, Nishikyo, Kyoto 615 8510, Japan
    Chem Commun (Camb) 48:5076-8. 2012
    ..This method provides a novel enantioselective route to β-hydroxy carboxyl compounds, which in turn can be used to synthesize valuable chiral building blocks...
  7. doi request reprint Nickel-catalyzed cycloaddition of salicylic acid ketals to alkynes via elimination of ketones
    Akihiro Ooguri
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615 8510, Japan
    J Am Chem Soc 131:13194-5. 2009
    ..A mechanistic rationale is proposed, implying beta-elimination of ketone from ring strained seven-membered nickelacycle to generate a five-membered oxa-nickelacycle intermediate...
  8. doi request reprint Silver-catalyzed intramolecular chloroamination of allenes: easy access to functionalized 3-pyrroline and pyrrole derivatives
    Masahiro Sai
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto Daigaku Katsura, Nishikyo ku, Kyoto 615 8510, Japan
    Org Lett 13:4676-9. 2011
    ..The chloroamination products are useful synthetic intermediates and can be easily transformed into functionalized 3-pyrroline and pyrrole derivatives...
  9. doi request reprint Nickel-catalyzed [4 + 2] cycloaddition of enones with alkynes
    Ichiro Koyama
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615 8510, Japan
    J Am Chem Soc 131:1350-1. 2009
    ..A mechanistic rationale is proposed, implying oxa-nickela cycle formation by oxidative cyclization of nickel to enone, followed by alkyne insertion...
  10. doi request reprint Nickel-catalyzed cycloaddition of anthranilic acid derivatives to alkynes
    Nobuyoshi Maizuru
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto, Japan
    Org Lett 13:1206-9. 2011
    ..The reaction involves oxidative addition of Ni(0) to an ester moiety, which allows intermolecular addition to alkynes via decarbonylation and 1,3-acyl migration...
  11. ncbi request reprint Cobalt(III) porphyrin catalyzed aza-Diels-Alder reaction
    Ryota Wakabayashi
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615 8510, Japan
    Org Lett 14:4794-7. 2012
    ..Highly chemoselective cycloaddition of imines with dienes in the presence of a variety of carbonyl compounds was also demonstrated...
  12. doi request reprint A tandem reaction initiated by 1,4-addition of bis(iodozincio)methane for 1,3-diketone formation
    Mutsumi Sada
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoutodaigaku katsura, Nishikyo, Kyoto 615 8510, Japan
    J Am Chem Soc 132:432-3. 2010
    ..The overall reaction gives 1,3-diketones efficiently...
  13. doi request reprint Asymmetric catalytic cycloetherification mediated by bifunctional organocatalysts
    Keisuke Asano
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigaku katsura, Nishikyo, Kyoto 615 8510, Japan
    J Am Chem Soc 133:16711-3. 2011
    ..This catalytic process represents a highly practical cycloetherification method that provides excellent enantioselectivities, even with low catalyst loadings at ambient temperature...
  14. doi request reprint Nickel-iminophosphine-catalyzed [4+2] cycloaddition of enones with allenes: synthesis of highly substituted dihydropyrans
    Saori Sako
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615 8510, Japan
    Chem Commun (Camb) 47:6150-2. 2011
    ..Enones were found to react with allenes intermolecularly in the presence of a catalytic amount of a nickel-iminophosphine complex to provide dihydropyrans via oxidative cyclization of an enone and Ni(0)...
  15. ncbi request reprint Transition-metal-catalyzed sequential cross-coupling of bis(iodozincio)methane and -ethane with two different organic halides
    Hideaki Yoshino
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoudai katsura, Nishikyo, Japan
    Chemistry 12:721-6. 2006
    ..Bis(iodozincio)ethane can also undergo this transformation, yielding a new stereogenic center. The asymmetric induction of this stereogenic center was investigated by using a chiral palladium catalyst...
  16. ncbi request reprint Preparation of enolate-homoenolate species as (Z)-gamma-siloxyallylmetal equivalents: sequential 1,4-addition of bis(iodozincio)methane to 1,4-dicarbonylbutenes and cyclopropanation
    Takaharu Hirayama
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoutodaigaku katsura, Nishikyo, Kyoto 615 8501, Japan
    Angew Chem Int Ed Engl 44:3293-6. 2005
  17. doi request reprint Nickel-catalyzed decarbonylative addition of anhydrides to alkynes
    Yuichi Kajita
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615 8510, Japan
    J Am Chem Soc 130:17226-7. 2008
    ..A mechanistic rationale is proposed, implying reductive elimination of Ni(0) promoted by ZnCl(2) cocatalyst as the key step of the catalytic cycle...
  18. ncbi request reprint Stereocontrolled addition of enolates to chiral 2-acyl-1,3-oxathiane derivatives
    Seijiro Matsubara
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Yoshida, Kyoto, Japan
    Chirality 15:38-40. 2003
    ....
  19. ncbi request reprint Stereospecific and stereoselective preparation of 2-(1-hydroxyalkyl)-1-alkylcyclopropanols from alpha,beta-epoxy ketones and bis(iodozincio)methane
    Kenichi Nomura
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoutodaigaku katsura, Nishikyo, Kyoto 615 8501, Japan
    Angew Chem Int Ed Engl 44:5860-3. 2005
  20. ncbi request reprint Nickel-catalyzed intermolecular codimerization of acrylates and alkynes
    Hiroaki Horie
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615 8510, Japan mbox media kyoto u ac jp
    Chem Commun (Camb) 47:2658-60. 2011
    ..The linear codimerization of acrylates and alkynes to produce 1,3-dienes is successfully demonstrated using a nickel catalyst in association with 2-aminopyridine as an additive...
  21. ncbi request reprint Methylenecyclopropanes in [4+1] cycloaddition with enones
    Tasuku Inami
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615 8510, Japan
    Org Lett 13:3837-9. 2011
    ..The reaction outcome is attributed to the transformation of methlenecyclopropane, which is incorporated into a five-membered ring as a one-carbon fragment...
  22. ncbi request reprint Preparation and reaction of 2-aryl-3-silyl-1,3-butadiene
    Zenichi Ikeda
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoutodaigaku katsura, Nishikyo, Japan
    Org Lett 7:4859-61. 2005
    ..A subsequent cross-coupling reaction of the product with another aryl halide gave an unsymmetrical 2,3-diaryl-1,3-butadiene efficiently...
  23. ncbi request reprint Platinum(IV) oxide catalyzed H-D exchange reactions in arylsilanes
    Mitsuru Yamamoto
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoudai katsura, Nishikyo, Kyoto 615 8510, Japan
    Org Lett 6:5015-7. 2004
    ..Arylsilanols were also labeled with regioselectively under the same conditions...
  24. ncbi request reprint A tandem reaction of organozinc reagent prepared from palladium-catalyzed umpolung method: diastereoselective formation of cyclohexene derivatives bearing three adjacent stereocenters
    Mutsumi Sada
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoutodaigaku katsura, Nishikyo, Kyoto 615 8510, Japan
    Org Biomol Chem 9:1389-93. 2011
    ..Thus formed zinc species afforded a cyclohexene derivative via a self-condensation reaction. It is noteworthy that the three adjacent stereogenic centers were created in a single process with quite high diastereoselectivity...
  25. ncbi request reprint Manganese porphyrin catalyzed cycloisomerization of enynes
    Takuya Ozawa
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615 8510, Japan
    Org Lett 14:3008-11. 2012
    ..The axial ligand of the catalyst has a marked effect on the product and selectively aids the formation of five- or six-membered cyclic products...
  26. ncbi request reprint Nickel-catalyzed [4+2] cycloaddition for highly substituted arenes
    Hiroaki Horie
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615 8510, Japan
    Chem Commun (Camb) 48:3866-8. 2012
    ..This formal inverse electron-demand Diels-Alder cycloaddition is attributed to the formation of a seven-membered nickelacycle from a diene and an alkyne...
  27. ncbi request reprint Cationic iron(III) porphyrin-catalyzed [4 + 2] cycloaddition of unactivated aldehydes with simple dienes
    Kyohei Fujiwara
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto, Japan
    J Am Chem Soc 134:5512-5. 2012
    ..Further, the potential utility of the catalyst was demonstrated by performing the cycloaddition in the presence of water and by carrying out cycloaddition of an unactivated ketone such as cyclohexanone with a diene...
  28. ncbi request reprint Methylenecyclopropane as C1 synthetic units: [1+4] cycloaddition via a nickel catalyst
    Tasuku Inami
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615 8510, Japan
    Chem Commun (Camb) 47:9711-3. 2011
    ..The reactions represent a new use for methylenecyclopropane as a possible one-carbon building block to replace carbon monoxide, isocyanides, and Fischer carbene complexes...
  29. ncbi request reprint Dehydrogenative Diels-Alder reaction
    Takuya Ozawa
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615 8510, Japan
    Org Lett 13:5390-3. 2011
    ..It was found that a key requirement of this process is the presence of a silyl group attached to the alkyne moiety, which forces a dehydrogenation reaction to occur...
  30. ncbi request reprint Nickel-catalyzed cycloaddition of o-arylcarboxybenzonitriles and alkynes via cleavage of two carbon-carbon σ bonds
    Kenichiro Nakai
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615 8510, Japan
    J Am Chem Soc 133:11066-8. 2011
    ..The reaction process displays an unusual mechanistic feature-the cleavage of two independent C-CN and C-CO bonds...
  31. ncbi request reprint Nucleophilic Cyclopropanation Reaction with Bis(iodozincio)methane by 1,4-Addition to alpha,beta-Unsaturated Carbonyl Compounds
    Kenichi Nomura
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoutodaigaku katsura, Nishikyo ku, Kyoto 615 8510 Japan, Fax 81 75 383 2463
    Chem Asian J 4:1298-303. 2009
    ..Additionally, reaction of the obtained homoenolate equivalents with imines give 1-(E)-alkenyl-2-(1-aminoalkyl)alkanols diastereoselectively...
  32. ncbi request reprint Selective synthesis of trienes and dienes via nickel-catalyzed intermolecular cotrimerization of acrylates and alkynes
    Hiroaki Horie
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615 8510, Japan
    Chem Commun (Camb) 46:7229-31. 2010
    ..Tailoring nickel-catalyzed linear cotrimerization of acrylates and alkynes effectively proceeds to produce trienes and dienes highly selectively...
  33. ncbi request reprint Nickel-catalyzed cycloadditions of thiophthalic anhydrides with alkynes
    Tasuku Inami
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615 8510, Japan
    Org Lett 13:1912-5. 2011
    ..Selective formations of thioisocoumarins, benzothiophenes, and thiochromones were accomplished with three different reaction conditions...
  34. doi request reprint Procedure-controlled enantioselectivity switch in organocatalytic 2-oxazolidinone synthesis
    Yukihiro Fukata
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigaku katsura, Nishikyo, Kyoto 615 8510, Japan
    J Am Chem Soc 135:12160-3. 2013
    ....
  35. ncbi request reprint Dynamic motion of building blocks in porous coordination polymers
    Satoshi Horike
    Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo ku, Kyoto 615 8510, Japan
    Angew Chem Int Ed Engl 45:7226-30. 2006
  36. ncbi request reprint Nickel-catalyzed decarboxylative carboamination of alkynes with isatoic anhydrides
    Yasufumi Yoshino
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615 8510, Japan
    J Am Chem Soc 131:7494-5. 2009
    ..A mechanistic rationale is proposed, implying oxidative addition of Ni(0) to a carbamate, which allows intermolecular addition to alkynes via decarboxylation...
  37. ncbi request reprint 1,4-Addition of bis(iodozincio)methane to α,β-unsaturated ketones: chemical and theoretical/computational studies
    Mutsumi Sada
    Department of Material Chemistry, Graduate School of Engineering, Kyoudai katsura, Nishikyo, Kyoto 615 8510, Japan
    Chemistry 16:10474-81. 2010
    ..A theoretical/computational study indicates that the whole reaction pathway is exothermic, and that two zinc atoms of bis(iodozincio)methane accelerate each step cooperatively as effective Lewis acids...
  38. ncbi request reprint A new zincate-mediated rearrangement reaction of 2-(1-hydroxyalkyl)-1-alkylcyclopropanol
    Kenichi Nomura
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoutodaigaku katsura, Nishikyo ku, Kyoto 615 8510, Japan
    Chemistry 16:703-8. 2010
    ..When bicyclo[13.1.0]pentadecane-1,15-diol was treated with the organozinc ate complex, the corresponding 14-membered cyclic vic-diol was obtained. Thus, this rearrangement is also useful for changing the ring size of cyclic substrates...
  39. ncbi request reprint Stereospecific Construction of Chiral Tertiary and Quaternary Carbon by Nucleophilic Cyclopropanation with Bis(iodozincio)methane
    Kenichi Nomura
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoutodaigaku katsura, Nishikyo ku, Kyoto 615 8510 Japan, Fax 81 75 383 2463
    Chem Asian J 5:147-52. 2010
    ..When it is treated with an electrophile in the presence of copper cyanide, it gives an optically active alpha-tertiary or -quaternary ketone that retains high optical purity...
  40. ncbi request reprint Decarbonylative cycloaddition of phthalic anhydrides with allenes
    Yosuke Ochi
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615 8510, Japan
    Org Lett 13:1374-7. 2011
    ..The asymmetric variant of the cycloaddition was also achieved by using chiral phosphine ligands to provide δ-lactones enantioselectively...
  41. ncbi request reprint Decarbonylative cycloaddition of phthalimides with 1,3-dienes
    Kyohei Fujiwara
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615 8510, Japan
    Org Lett 12:4548-51. 2010
    ..The decarbonylative cycloadditions of phthalimides with 1,3-dienes were performed by using nickel catalyst. The reactions afford 3-vinyldihydroisoquinolones regioselectively with respect to both 1,3-dienes and phthalimides...
  42. ncbi request reprint Nickel-catalyzed [2+2+1] cycloaddition of alkynes, acrylates and isocyanates
    Takuya Ozawa
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615 8510, Japan
    Chem Commun (Camb) 46:8055-7. 2010
    ..Intermolecular [2+2+1] cycloaddition which incorporates an alkyne, an isocyanate, and an alkene into a γ-butyrolactam proceeds with nickel catalyst...
  43. ncbi request reprint Preparation of a cycloheptane ring from a 1,2-diketone with high stereoselectivity
    Yoshiaki Takada
    Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoudai katsura, Nishikyo, Kyoto 615 8510, Japan
    Org Lett 12:5204-5. 2010
    ..Bis(iodozincio)methane converted the diketone into the cis-divinylcyclopropane-1,2-diol stereoselectively; this diol transformed into the corresponding cycloheptane derivative stereospecifically via Cope rearrangement...