0000000001309451

AUTHOR

Akihiro Shimizu

showing 7 related works from this author

Metal‐Free Twofold Electrochemical C−H Amination of Activated Arenes: Application to Medicinally Relevant Precursor Synthesis

2020

Abstract The efficient production of many medicinally or synthetically important starting materials suffers from wasteful or toxic precursors for the synthesis. In particular, the aromatic non‐protected primary amine function represents a versatile synthetic precursor, but its synthesis typically requires toxic oxidizing agents and transition metal catalysts. The twofold electrochemical amination of activated benzene derivatives via Zincke intermediates provides an alternative sustainable strategy for the formation of new C−N bonds of high synthetic value. As a proof of concept, we use our approach to generate a benzoxazinone scaffold that gained attention as a starting structure against ca…

Green chemistrydrug scaffoldPrimary (chemistry)Full Paper010405 organic chemistryChemistrybenzoxazinoneOrganic ChemistryGeneral ChemistryFull Papers010402 general chemistryElectrochemistry01 natural sciencesCombinatorial chemistryCatalysis0104 chemical sciencesCatalysiselectrochemistrytwofold aminationMetal freeOxidizing agentsustainable chemistryAmine gas treatingSynthetic MethodsAminationChemistry – A European Journal
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New Approach to 1,4-Benzoxazin-3-ones by Electrochemical C-H Amination.

2017

1,4-Benzoxazin-3-ones are important structural motifs in natural products and bioactive compounds. Usually the synthesis of benzoxazinones requires transition metal catalysts and pre-functionalized substrates, e.g. aryl halides. However, the anodic C,H amination of phenoxy acetates offers a very efficient and sustainable access to these heterocycles. The herein presented electrochemical protocol can be applied to a broad scope of alkylated substrates. Even tert-butyl moieties or halogen substituents are compatible with this versatile method.

Green chemistry010405 organic chemistryBenzoxazinonesArylOrganic ChemistryHalideGeneral ChemistryAlkylation010402 general chemistry01 natural sciencesCatalysis0104 chemical sciencesCatalysischemistry.chemical_compoundchemistryHalogenOrganic chemistryAminationChemistry (Weinheim an der Bergstrasse, Germany)
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Cover Feature: New Approach to 1,4-Benzoxazin-3-ones by Electrochemical C−H Amination (Chem. Eur. J. 50/2017)

2017

Green chemistryFeature (computer vision)ChemistryOrganic ChemistryCover (algebra)General ChemistryElectrochemistryCombinatorial chemistryCatalysisAminationChemistry - A European Journal
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CCDC 1998477: Experimental Crystal Structure Determination

2021

Related Article: Lars J. Wesenberg, Erika Diehl, Till J. B. Zähringer, Carolin Dörr, Dieter Schollmeyer, Akihiro Shimizu, Jun‐ichi Yoshida, Ute A. Hellmich, Siegfried R. Waldvogel|2020|Chem.-Eur.J.|26|17574|doi:10.1002/chem.202003852

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameters5-fluoro-2-methoxy-N-(6-methoxy-22-dimethyl-3-oxo-34-dihydro-2H-14-benzoxazin-7-yl)benzene-1-sulfonamideExperimental 3D Coordinates
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CCDC 1998478: Experimental Crystal Structure Determination

2021

Related Article: Lars J. Wesenberg, Erika Diehl, Till J. B. Zähringer, Carolin Dörr, Dieter Schollmeyer, Akihiro Shimizu, Jun‐ichi Yoshida, Ute A. Hellmich, Siegfried R. Waldvogel|2020|Chem.-Eur.J.|26|17574|doi:10.1002/chem.202003852

2-methoxy-N-(6-methoxy-22-dimethyl-3-oxo-34-dihydro-2H-14-benzoxazin-7-yl)-5-methylbenzene-1-sulfonamideSpace GroupCrystallographyCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
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CCDC 1998475: Experimental Crystal Structure Determination

2021

Related Article: Lars J. Wesenberg, Erika Diehl, Till J. B. Zähringer, Carolin Dörr, Dieter Schollmeyer, Akihiro Shimizu, Jun‐ichi Yoshida, Ute A. Hellmich, Siegfried R. Waldvogel|2020|Chem.-Eur.J.|26|17574|doi:10.1002/chem.202003852

Space GroupCrystallographyCrystal System7-amino-6-methoxy-22-dimethyl-2H-14-benzoxazin-3(4H)-oneCrystal StructureCell ParametersExperimental 3D Coordinates
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CCDC 1998476: Experimental Crystal Structure Determination

2021

Related Article: Lars J. Wesenberg, Erika Diehl, Till J. B. Zähringer, Carolin Dörr, Dieter Schollmeyer, Akihiro Shimizu, Jun‐ichi Yoshida, Ute A. Hellmich, Siegfried R. Waldvogel|2020|Chem.-Eur.J.|26|17574|doi:10.1002/chem.202003852

5-bromo-2-methoxy-N-(6-methoxy-22-dimethyl-3-oxo-34-dihydro-2H-14-benzoxazin-7-yl)benzene-1-sulfonamideSpace GroupCrystallographyCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
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