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Synthetic Methods for Redox Reactions Using Phosphorus, Vanadium and Samarium Compounds

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Functionalized Redox Systems

Abstract

The tautomerism of dialkyl phosphonate between P(III) and P(V) species is applied to a variety of synthetic transformations, including reductive dehalogenation and palladium-catalyzed phophonation. Low-valent vanadiums contribute to reductive transformations as observed in catalytic reduction of organic halides. Catalytic pinacol coupling reaction is induced by vanadiums or titaniums in the presence of a chlorosilane and a co-reductant zinc. Use of the heterobimetallic catalyst permits the selective cross-coupling. Samarium(II) compounds are also used for the reduction reactions. Using Lewis acidity with one-electron oxidation capability of oxovanadium(V) compounds, oxidative transformations of carbonyl compounds are developed. Silyl enol ethers and boron enolates undergo selective oxidative coupling. Organic substituents of main-group organometallic compounds are coupled by oxidation with oxovanadium(V) compounds to give ligand coupling products. Bio-inspired and environmentally harmonic vanadium-catalyzed halogenation is attained in the presence of halide anion and Lewis or Brønsted acid under molecular oxygen to give halogenated compounds.

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Abbreviations

acac:

Acetylacetonate

2-BPEPA:

N,N′-Bis[2-(2-pyridyl)ethyl]-2,6-pyridinedicarboxamide

BIPA:

N,N′-Bis[2-(4-imidazolyl)ethyl]-2.6-pyridinedicarboxamide

CAN:

Cerium(IV) ammonium nitrate

DIPHOS:

1,2-Bis(diphenylphosphino)ethane

DME:

1,2-Dimethoxyethane

Et:

Ethyl

HMPA:

Hexamethylphosphoramide

L:

Liter(s)

Me:

Methyl

MeCN:

Acetonitrile

mol:

Mole(s)

Ph:

Phenyl

PTS•H2O:

p-Toluenesulfonic acid monohydrate

TBS:

tert-Butyldimethylsilyl

TFA:

Trifluoroacetic acid

THF:

Tetrahydrofuran

VBrPO:

Vanadium bromoperoxidase

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Authors and Affiliations

  1. Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamada-oka, Suita, Osaka, 565-0871, Japan

    Toshikazu Hirao, Toshiyuki Moriuchi & Toru Amaya

  2. Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Naka-ku, Sakai, Osaka, 599-8531, Japan

    Akiya Ogawa & Akihiro Nomoto

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    Toshikazu Hirao

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Hirao, T., Moriuchi, T., Amaya, T., Ogawa, A., Nomoto, A. (2015). Synthetic Methods for Redox Reactions Using Phosphorus, Vanadium and Samarium Compounds. In: Hirao, T. (eds) Functionalized Redox Systems. Springer, Tokyo. https://doi.org/10.1007/978-4-431-55306-9_2

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