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5 article(s) from Okada, Yohei

Electrochemical radical cation aza-Wacker cyclizations

Sota Adachi and
Yohei Okada

Beilstein J. Org. Chem. 2024, 20, 1900–1905, doi:10.3762/bjoc.20.165

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Scheme 1: Radical and ionic intramolecular cyclizations.

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Scheme 2: Electrochemical and photochemical aza-Wacker cyclizations.

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Scheme 3: Scope of electrochemical aza-Wacker cyclization. Reaction conditions: the alkene (0.20 mmol), Bu₄NO...

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Scheme 4: Mechanistic studies of aza-Wacker cyclization. A: Electrochemical (Bu₄NOTf in CH₃CN/1,2-DCE), B: no...

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Figure 1: Cyclic voltammograms for aryl sulfonamides.

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Letter

Published 05 Aug 2024

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Radical cation Diels–Alder reactions of arylidene cycloalkanes

Kaii Nakayama,
Hidehiro Kamiya and
Yohei Okada

Beilstein J. Org. Chem. 2022, 18, 1100–1106, doi:10.3762/bjoc.18.112

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Figure 1: Plausible mechanism of the radical cation Diels–Alder reaction (EDG: electron-donating group).

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Figure 2: Landscape of the radical cation Diels–Alder reaction.

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Scheme 1: Radical cation Diels–Alder reaction of β-methylstyrene.

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Scheme 2: Radical cation Diels–Alder reaction of β-methylanethole (1). Recovered starting material is reporte...

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Figure 3: Formal expression of radical cations.

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Scheme 3: Radical cation Diels–Alder reactions of the arylidene cycloalkanes (4–7). Recovered starting materi...

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Scheme 4: Scope of the radical cation Diels–Alder reaction of arylidene cycloalkanes (recovered starting mate...

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Letter

Published 25 Aug 2022

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Artificial bioconjugates with naturally occurring linkages: the use of phosphodiester

Takao Shoji,
Hiroki Fukutomi,
Yohei Okada and
Kazuhiro Chiba

Beilstein J. Org. Chem. 2018, 14, 1946–1955, doi:10.3762/bjoc.14.169

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Figure 1: Schematic illustration of possible support-assisted methods.

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Figure 2: Expected reactivity of 5’- and 3’-terminus for the activation.

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Scheme 1: Competition experiment between alcohol and carboxylic acid. Reagents and conditions: (i) 4-phenylbu...

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Scheme 2: Conjugation between the 5’-activated supported trinucleotide 2 and the tripeptide 3. Reagents and c...

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Figure 3: HPLC spectra of the crude protected bioconjugate 4 and the crude deprotected bioconjugate 5.

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Scheme 3: 5’-Phosphitylation of supported decanucleotide 13. Reagents and conditions: 2-cyanoethyl-N,N,N',N'-...

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Scheme 4: Conjugation between 5’-activated supported decanucleotide 14 and supported pentapeptide 7. Reagents...

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Figure 4: HPLC spectra of the crude protected bioconjugate 15 and the deprotected bioconjugate 16.

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Full Research Paper

Published 27 Jul 2018

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Stepwise radical cation Diels–Alder reaction via multiple pathways

Ryo Shimizu,
Yohei Okada and
Kazuhiro Chiba

Beilstein J. Org. Chem. 2018, 14, 704–708, doi:10.3762/bjoc.14.59

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Scheme 1: Radical cation Diels–Alder reaction of trans-anethole [17].

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Scheme 2: Radical cation Diels–Alder reactions of aryl vinyl ether and sulfides [17,25].

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Scheme 3: Radical cation Diels–Alder reaction of aryl vinyl ether (1). Conditions: 1.0 M LiClO₄/CH₃NO₂, carbo...

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Scheme 4: Oxidative SET-triggered reaction of aryl vinyl ether 1_c. Conditions: 1.0 M LiClO₄/CH₃NO₂, carbon fe...

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Figure 1: GC–MS Monitoring of the oxidative SET-triggered reaction of aryl vinyl ether 1_c.

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Scheme 5: Oxidative SET-triggered rearrangement of vinyl cyclobutane 4. Conditions: 1.0 M LiClO₄/CH₃NO₂, carb...

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Scheme 6: Unsuccessful rearrangement of cyclobutanes. Conditions: 1.0 M LiClO₄/CH₃NO₂, carbon felt electrodes...

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Scheme 7: Proposed mechanism for the radical cation Diels–Alder reaction of aryl vinyl ether 1.

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Letter

Published 27 Mar 2018

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Investigating radical cation chain processes in the electrocatalytic Diels–Alder reaction

Yasushi Imada,
Yohei Okada and
Kazuhiro Chiba

Beilstein J. Org. Chem. 2018, 14, 642–647, doi:10.3762/bjoc.14.51

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Scheme 1: SET-triggered Diels–Alder reaction of trans-anethole (1) and isoprene (2).

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Figure 1: Plausible mechanism for the electrocatalytic Diels–Alder reaction. Adapted from [22].

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Scheme 2: Undesired dimerization of trans-anethole (1).

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Figure 2: GC–MS monitoring of the electrocatalytic Diels–Alder reaction (1: 300 mM; 2: 3000 mM).

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Figure 3: GC–MS monitoring of the electrocatalytic Diels–Alder reaction (1: 1 mM; 2: 2000 mM).

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Figure 4: GC–MS monitoring of the electrocatalytic Diels–Alder reaction (1: 2 M; 2: 6 M). Blue dots show the ...

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Letter

Published 16 Mar 2018

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