神奈川大学 化学生命学部 生命機能学科 岡本専太郎研究室 有機反応デザイン研究室
神奈川大学 化学生命部 生命機能学科 岡本専太郎研究室


I




研究紹介インタビュー動画  Research Introduction (OKA interview)



YouTube Link


クリックで再生できな場合は,「別タグ」開いて下さい。
When you cannot play by clicking, please open this with "another tag".
  

内閣府 CSTI 「こんな研究をして世界を変えようURLリンク

リクルート 夢ナビ URLリンク

神大の先生 URLリンク


東洋経済 MOOK本で生物学教室の中川先生との共同研究が
取り挙げられました。
 記事はこちら=>
    

ページの先頭へ

Recent Works

Ti chemistry

S. Okamoto, T. Yamada, T. Uchida, N. Kikuta, and Y. Kimura
"Dual-Mode Coupling Copolymerization of Aryl Dialdehyde and Alkynylaldehyde Monomers via Concurrent McMurry Olefination and Alkyne [2+2+2] Cycloaddition Trimerization Reactions Mediated by a Low-Valent Titanium Reagent",
Polymer, 2021, 214, 123344.
[Link]


Kouta Ibe, Takeshi, Yamada, Sentaro Okamoto,
"Synthesis and Vitamin D Receptor Affinity of 16-Oxa Vitamin D3 Analogues", Organic & Biomolecular Chemistry, 2019, 17, 10188-10200.
[Link]


Sentaro Okamoto, Takeshi Yamada, Yu-ki Tanabe, Masaki Sakaia
"Alkyne [2+2+2] Cyclotrimerization Catalyzed by a Low-Valent Titanium Reagent Derived from CpTiX3 (X = Cl, O-i-Pr), Me3SiCl, and Mg or Zn”,
Organomettalics, 2018, 37, 4431-4438.
[Link]


Suchithra Madhavan, Hiromasa Takagi, Shunpei Fukuda and Sentaro Okamoto, "Low−valent titanium−catalyzed deprotection of allyl- and propargyl-carbamates to amines”,
Tetrahedron Letters, 2016, 57, 2074-2077.
[Link]



Sentaro Okamoto, “Synthetic Reactions Using Low-Valent Titanium Reagents Derived from Ti(OP)4 or CpTiX3 (X = O-i-Pr or Cl) in the Presence of Me3SiCl and Mg”,
The Chemical Record, 2016, 16, 857-872

[Link]



Sentaro Okamoto, "Synthetic Reactions Using A Low-Valent Titanium Reagent Ti(OR)4/Me3SiCl/Mg,”
Yuki Gosei Kagaku Kyokaishi, 2014, 72, 382-392.



Generation of A Low-Valent Titanium from Titanatrane and Its Catalytic Reactions: Radical Ring Opening of Oxetanes
[Adv. Synth. Catal. 2013, 355, 2151-2157]



Non-Cp Titanium Alkoxide-Based Homolytic Ring-Opening of Epoxides by An Intramolecular Hydrogen Abstraction in beta-Titanoxy Radical Intermediates
[Chemical Communications, 2011, 47, 7857-7859.]



Ti(O-i-Pr)4/Me3SiCl/Mg-Mediated Reductive Cleavage of Sulfonamides and Sulfonates To Amines and Alcohols
[Organic Letters, 2011, 13, 2626-2629.]
Highlighted in Organic Chemistry Highlights. Highlighted in Organic Chemistry Portal Picked up in ChemInform



McMurry coupling of aryl aldehydes and imino pinacol coupling mediated by Ti(O-i-Pr)4/Me3SiCl/Mg reagent
[Tetrahedron Letters, 2010, 51, 387-390]
Picked up by SYNFACTS(2010, p 346



Two-step allylic carbon insertion between ketone carbonyl and carbons giving a-quaternary a-vinyl ketones
[Tetrahedron Letters, 2008, 49, 6724-6727]
Picked up in ChemInform



Selective Cleavage of Allyl and Propargyl Ethers to Alcohols Catalyzed by Ti(O-i-Pr)4/MXn/M
[Organic Letters, 2007, 9, 773-776]
Picked up in ChemInform



Ti(II)-Mediated domino cyclization of 2-functionalized 1-halo-2,n-enynes (n = 7, 8) to bicyclic compounds
[Tetrahedron Letters, 2006, 47, 7537-7540]
Picked up in ChemInform



Synthesis of N-substituted 2-arylpyrroles by the reaction of (eta2-imine)titanium complexes with 3,3-diethoxypropyne
[Tetrahedron Letters, 2006, 47, 6209-6212]
Highlighted in SYNFACTS(2006, p.1223)



Formation of azatitanacyclopentanes from ene-imines and a Ti(O-i-Pr)4/2i-PrMgX reagent and their synthetic reactions
[Tetrahedron Lettrs, 2004, 45, 9037-9040]
Picked up in ChmeInform

Fe, Co, Ni catalysis

Yu-ki Sugiyama, Masaki Amo, Kouta Ibe, and Sentaro Okamoto
"Synthesis of 2-Aminopyridines via Cobalt-Catalyzed Cycloaddition of Diynes with N-Substituted and N-Unsubstituted Cyanamides",
Adv. Synth. Catal., 2023, 365, 3897-3901. [Link]open access


Yuhsaku Okabe, Takeshi Yamada, and Sentaro Okamoto
"Nickel-Catalysed Cycloaddition Oligomerization of 1,6-Diynes to Medium-Size Cyclic Polyenes",
Polymer Chemistry, 2022, 13, 6075-6172. [Link]


Nana Kikuta, Takahiro Shindo, Yu-ki Sugiyama, Takeshi Yamada
and Sentaro Okamoto
Cobalt-Catalyzed [2 + 2 + 2] Cycloaddition Copolymerization of Diyne and Internal Alkyne Monomers to Highly Branched Polymers
Polymer, 2021, 212, 123133.[Link]


Yu-ki Sugiyama, Shiori Heigozono, Kazuhiro Tamura, Sentaro Okamoto, "Iron-Catalyzed Reductive Metalation–Allylation and Metalative Cyclization of 2,3-Disubstituted Oxetanes and Their Stereoselectivity”,
Synthesis, 2016, 48, 2823-2828.[Link]



Catalytic [2 + 2 + 2] Cycloaddition Polymerization of Diyne–Nitrile Monomers in the Presence of CoCl2-6H2O/Diphosphine/Zn

J. Polym. Sci. A: Polym. Chem. 2016, 54, 345-351..


Iron-Catalyzed Reductive Magnesiation of Oxetanes to Gen-erate (3-Oxidopropyl)magnesium Reagents
Org. Lett. 2014, 16,6278-6281.


Cobalt-Catalyzed Cross Addition of Silylacetylenes to Internal Alkynes,
[J. Org. Chem. 2013, 78, 3583-3591]



From Development of Catalysts for Alkyne and Alkyne/Nitrile [2 + 2 + 2] Cycloaddition Reactions to Their Use in Polymerization Reactions,
[Synlett, 2013, 1044-1060] (Account)



Remarkable Activation of An Alkyne [2 + 2 + 2] Cycloaddition Catalyst, 2-Iminomethylpyridine (Dipimp)/CoCl2-6H2O/Zn, by a Phthalate Additive
[SYNLETT 2012, 23, 2549-2553]



Synthesis of 2,2’-Bipyridines by Transition Metal-Catalyzed Alkyne/Nitrile [2 + 2 + 2] Cycloaddition Reactions
[Review in: Heterocycles, Heterocycles, 2012, 85, 1579-1602.]



Chain-Growth Cycloaddition Polymerization via a Catalytic Alkyne [2 + 2 + 2] Cyclotrimerization Reaction and Its Application to One-shot Spontaneous Block Copolymerization
[J. Am. Chem. Soc. 2011, 133, 9712-9715.]
Highlighted in ACS Noteworthy Chemistry and Selected as SYNFACT of the month



Regioselective Synthesis of Substituted Pyridines and 2,2'-Dipyridines by a Cobalt-Catalyzed [2 + 2 + 2] Cycloaddition of a,w-diynes with Nitriles
[Synthesis 2011, 2247-2254.] (special issue) See also the Correction: Errata (2011, 3928)
Picked up in ChemInform



Quick Access to Diverse Polymerizable Molecules (a Monomer Library) by Catalytic [2 + 2 + 2] Cycloaddition Reactions of Functionalized Alkynes
[ Macromolecules, 2010, 43, 2213-2218 ]


Synthesis of substituted anthracenes, pentaphenes and trinaphthylenes via alkyne cyclotrimerization reaction
[Tetrahedron Letters, 2010, 51, 1313-1316.]
Picked up in SYNFACTS(2010, p 423)



Selective Dimerization of 1,6-Diynes Catalyzed by Ionic Liquid-Supported Nickel Complexes in An Ionic Liquid/Toluene Biphasic System,
[Chem. Commun. 2009, 439-441.]
Picked up by SYNFACTS(2009, p 458 and ChemInform



Synthesis of Substituted 2,2'-Bipyridines and 2,2':6,2"-Terpyridines by Cobalt-Catalyzed Cycloaddition Reactions of Nitriles and a,w-Diynes with Exclusive Regioselectivity,
[Advanced Synthesis & Catalysis, 2008, 350, 143-152.]
Picked up in ChemInform



Efficient Activation of 2-Iminomethylpyridine/Cobalt-Baesd Alkyne [2 + 2 + 2] Cycloaddition Catalyst by Addition of a Silver Salt
[Advanced Synthesis & Catalysis, 2007, 349, 2368-2374]



On-Demand Generation of an Efficient Catalyst for Pyridine Formation from Unactivated Nitriles and -Diynes Using CoCl2-6H2O, dppe and Zn
[Organic Letters, 2007, 9, 931-934]



Iron-catalyzed intramolecular cyclotrimerization of triynes to annulated benzenes
[J. Organometallic Chemistry, 2006, 691, 3129-3136]
Picked up in ChemInform



A Highly Practical Instant Catalyst for Cyclotrimerization of Alkynes to Substituted Benzenes
[Organic Letters, 2006, 8, 1439-1442]
Picked up in ChemInform



Cobalt-catalyzed benzyl-alkynyl coupling
[Tetrahedron Letters, 2006, 47, 2591-2594]
Picked up in ChemInform



Intramolecular Cyclotrimerization of Triynes Catalyzedby N-Heterocyclic Carbene-CoCl2/Zn or -FeCl3/Zn
[Organic Letters, 2005, 7, 3065-3067]
Picked up in ChemInform



Cobalt-catalyzed mono-coupling of R3SiCH2MgCl with 1,2-dihalogenoethylene: A general route to gamma-substituted (E)-allylsilanes
[Tetrahedron Letters, 2004, 45, 4677-4679]
Picked up in ChmeInform

Cu catalysis

Copper-catalyzed intramolecular hydroamination of allenylamines to 3-pyrrolines or 2-alkenylpyrrolidnes
[Tetrahedonr Letters 2008, 49, 6529-6532]
Picked up in ChmeInform



Allylic Substitution Reactions with Grignard Reagents Catalyzed by Imidazolium and 4,5-Dihydroimidazolium Carbene-CuCl Complexes
[J. Organometallic Chemistry, 2005, 690, 6001-6007 and see also Erratum]
Picked up in ChmeInform



gamma-Selective allylic substitution reaction with Grignard reagents catalyzed by copper N-heterocyclic carbene complexes and its application to enantioselective synthesis
[Tetrahedron Letters, 2004, 45, 5585-5588]
Picked up in ChmeInform

Other Metals

Silica-supported silver as a green and sustainable catalyst for [3+2] cycloaddition reaction of azomethine ylides with 2’-hydroxychalcone derivatives
[ChemCatChem, 2018, 10, 2014-2018.]



Grignard allylic substitution reaction catalyzed by 1,2,3-triazol-5-ylidene magnesium complexes
[Tetrahedron Letters, 2013, 54, 1360-1363]



Grignard allylic substitution catalyzed by imidazol-2-ylidene- and imidazol-4-ylidene-magnesium complexes
[Tetrahedron Letters, 2010, 51, 5704-5707]



Carbonyl reduction with CaH2 and R3SiCl catalyzed by ZnCl2"
[Tetrahedron Letters, 2007, 47, 9120-9123.]
Picked up in ChemInform



Use of CaH2 as a reductive hydride source: Reduction of ketones and imines with CaH2/ZnX2 in the presence of a Lewis acid
[Tetrahedron Letters, 2005, 46, 1667-1669]
Picked up in Best Synthetic Methods: Reduction in Organic Chemistry Highlights. Picked up in ChemInform

Non-metal Catalysis

Takeshi Yamada and Sentaro Okamoto,
"3,5,6-Trifluoro-2-pyridone effectively catalyses interrupted Passerini reaction of 3-(2- isocyanoethyl)-indole as a bifunctional catalyst. The described one-pot four-component coupling reaction enabled the rapid preparation of highly functionalised tetracyclic furoindolines",
Chem. Commun., 2022, 58, 11701-11704. [Link]open access


6-Halo-2-pyridone as an efficient organocatalyst for ester aminolysis
RSC Advances, 2021, 11, 24588-24593. [Link]open access



Simple and practical method for selective acylation of primary hydroxy group catalyzed by N-methyl-2-phenylimidazole (Ph-NMI) or 2-phenylimidazo[2,1-b]benzothiazoles (Ph-IBT)
[Tetrahedron Leetrs 2014, 55, 7039-7042.]


Structure–activity relationship of dihydroimidazo-, dihydropyrimido, tetrahydrodiazepino-[2,1-b]-thiazoles and -benzothiazoles as an acylation catalyst
[Tetrahedron Lett. 2014, 55, 1909-1912]



Synthesis and Catalytic Properties of 4-Aryl-2,3-dihydro-4H-pyrimido[2,3-b]benzothiazoles for Asymmetric Acyl or Carboxyl Group Transfer Reactions
[J. Org. Chem. 2011, 76, 6678-6685]
Picked up in ChemInform and Highlighted in Organic Chemistry Portal



Activity and behavior of imidazolium salts as a phase transfer catalyst for a liquid-liquid phase system
[Tetrahedron Letters, 2006, 47, 8055-8058]



Unexpected reactivity of annulated 3H-benzothiazol-2-ylideneamines as an acyl transfer catalyst
[Tetrahedron Letters, 2006, 47, 4347-4350]

Macromolecules

Yuhsaku Okabe, Takeshi Yamada, and Sentaro Okamoto
"Nickel-Catalysed Cycloaddition Oligomerization of 1,6-Diynes to Medium-Size Cyclic Polyenes",
Polymer Chemistry, 2022, 13, 6075-6172. [Link]


Sentaro Okamoto, Yusuke Naito, and Ryosuke Nomura
”Synthesis of Folded H-Stacking Skipped p Polymers Consisting of Different 2-Substituted Trimethylene Tethering Units and Their Optical and Conductive Property",
Polymer, 2021, 230, 124037. [Link]

S. Okamoto, T. Yamada, T. Uchida, N. Kikuta, and Y. Kimura
"Dual-Mode Coupling Copolymerization of Aryl Dialdehyde and Alkynylaldehyde Monomers via Concurrent McMurry Olefination and Alkyne [2+2+2] Cycloaddition Trimerization Reactions Mediated by a Low-Valent Titanium Reagent",
Polymer, 2021, 214, 123344.
[Link]


Nana Kikuta, Takahiro Shindo, Yu-ki Sugiyama, Takeshi Yamada
and Sentaro Okamoto
Cobalt-Catalyzed [2 + 2 + 2] Cycloaddition Copolymerization of Diyne and Internal Alkyne Monomers to Highly Branched Polymers
Polymer, 2021, 212, 123133.[Link]


Synthesis and properties of folded π-stacking polymers having J-aggregative, alternative, and staggered assembling structures
Polymer, 2016, 97, 550-558.
[Link]




Catalytic [2 + 2 + 2] Cycloaddition Polymerization of Diyne–Nitrile Monomers in the Presence of CoCl2-6H2O/Diphosphine/Zn

J. Polym. Sci. A: Polym. Chem. 2016, 54, 345-351.


Design and synthesis of 2-(1,3-dialkoxy-2-methylpropan-2-yl)-1,3-diarylpropanes as tethering units for folded H-stacking polymers
Tetrahedron Letters, 2014, 55, 2649-2653.


Synthesis and Properties of Through-Space Conjugated Polymers Based on pi–pi Stacked 1,3-Biarylpropane Tethering Units
[J. Polymer Science Part A: Polymer Chemistry, 2013, 51, 3412-3419]



Synthesis of [—CH2C(CO2Et)2CH2Ar—]n Polymers and Their Unique Optical Properties by Through-Space Interactions between Ar and C=O Groups
[J.Polymer Science Part A: Polymer Chemistry, 2012, 50, 1707-1716]



Chain-Growth Cycloaddition Polymerization via a Catalytic Alkyne [2 + 2 + 2] Cyclotrimerization Reaction and Its Application to One-shot Spontaneous Block Copolymerization
[J. Am. Chem. Soc. 2011, 133, 9712-9715.]
Highlighted in ACS Noteworthy Chemistry and Selected as SYNFACT of the month



Folded H-Stacking Polymers by Conformational Control with 2-Substituted Trimethylene Tethers
[Macromolecules, 2010, 43, 6562-6569.]



Quick Access to Diverse Polymerizable Molecules (a Monomer Library) by Catalytic [2 + 2 + 2] Cycloaddition Reactions of Functionalized Alkynes
[ Macromolecules, 2010, 43, 2213-2218 ]



Related to Synthesis of Biologically Active Compounds

Takeshi Yamada and Sentaro Okamoto,
"3,5,6-Trifluoro-2-pyridone effectively catalyses interrupted Passerini reaction of 3-(2- isocyanoethyl)-indole as a bifunctional catalyst. The described one-pot four-component coupling reaction enabled the rapid preparation of highly functionalised tetracyclic furoindolines",
Chem. Commun., 2022, accepted. [Link]open access


Kouta Ibe, Haruki Nakada, Mayu Ohgami, Takeshi Yamada, and Sentaro Okamoto,
"Design, Synthesis, and Properties of des-D-Ring Interphenylene Derivatives of 1α,25-Dihydroxyvitamin D3",
Eur. J. Med. Chem., 2022, 243, 114795. [Link]


Takeshi Yamada, Kazuki Arai, Rie Kikuchi and Sentaro Okamoto
”Deuteration of Indole Compounds: Synthesis of Deuterated Auxins, Indole-3-acetic Acid-d5 and Indole-3-butyric Acid-d5", ACS Omega, 2021, 6, 19956-19963.
[Link]open access


Kouta Ibe, Takeshi, Yamada, Sentaro Okamoto,
"Synthesis and Vitamin D Receptor Affinity of 16-Oxa Vitamin D3 Analogues", Organic & Biomolecular Chemistry, 2019, 17, 10188-10200.
[Link]


Preparation of 2-hydroxy A-ring precursors for synthesis of vitamin D3 analogues from lyxose
[Tetrahedron Lett. 2015, 56 ,2315-2318.]


Generation of A Low-Valent Titanium from Titanatrane and Its Catalytic Reactions: Radical Ring Opening of Oxetanes
[Adv. Synth. Catal. 2013, 355, 2151-2157]



Stereoselective construction of 3a-methylhydrindanes starting from 2,7-enynol derivatives based on Ti(II)-mediated cyclization and Ru-catalyzed ring-closing metathesis
[Tetrahedron Letters, 2006, 47, 5181-5185]
Picked up in ChemInform



Formation of azatitanacyclopentanes from ene-imines and a Ti(O-i-Pr)4/2i-PrMgX reagent and their synthetic reactions
[Tetrahedron Lettrs, 2004, 45, 9037-9040]
Picked up in ChmeInform


Previously Synthesized Compounds

関連リンクなどLinkIcon