Selective Anodic Fluorination of Electrophilic Alkenes.

Dinoiu, Vasile; Kanno, Kazuako; Fukuhara, Tsuyoshi; Yoneda, Norihiko

doi:10.1002/chin.200539050

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“…alkenes with the fluorinating agent Selectfluor in the presence of acetonitrile (Scheme 28), 154 in electrochemical fluorinations 155 and in the nitration of glucals (Scheme 28…”

Section: Syn Thesismentioning

confidence: 99%

Acetonitrile as a Building Block and Reactant

Hoff

2018

Synthesis

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Acetonitrile is popular as a solvent for performing organic reactions, as a ligand in inorganic chemistry, as a mobile phase in chromatography, and as an electrolyte solvent in dye-sensitized solar cells. This is mainly due to its ability to dissolve both polar and nonpolar components. However, acetonitrile is also a valuable building block allowing atom-efficient transformations in synthetic organic chemistry. The aim of this review is to highlight synthetic transformations using acetonitrile, covering both classical approaches and modern strategies proceeding through radical intermediates or mediated by metal catalysis. Besides showcasing synthetic protocols useful for acetonitrile and analogues, warnings for when not to use acetonitrile as a solvent are also provided.1 Introduction2 Fundamental Reactions with Acetonitrile3 Cyanomethylation of Non-Aromatics4 The Acetonitrile Nitrogen as a Nucleophile5 The Blaise Reaction6 Synthesis of Pyridines7 Other Cyclization Reactions8 Cyanomethylation of Arenes and Heteroarenes9 Acetylation of Arenes Using Acetonitrile10 Synthesis of N-Arylacetamides11 Cyanation Using Acetonitrile as a Cyanide Source12 When To Avoid Acetonitrile as a Solvent13 Conclusion

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“…alkenes with the fluorinating agent Selectfluor in the presence of acetonitrile (Scheme 28), 154 in electrochemical fluorinations 155 and in the nitration of glucals (Scheme 28…”

Section: Syn Thesismentioning

confidence: 99%

Acetonitrile as a Building Block and Reactant

Hoff

2018

Synthesis

View full text Add to dashboard Cite

show abstract

Selective Anodic Fluorination of Electrophilic Alkenes.

Abstract: Halogenation O 0235 Selective Anodic Fluorination of Electrophilic Alkenes. -(DINOIU*, V.; KANNO, K.; FUKUHARA, T.; YONEDA, N.; J. Fluorine Chem. 126 (2005) 5, 753-758; Div. Mol. Chem., Grad. Sch. Eng., Hokkaido Univ., Sapporo 060, Japan; Eng.) -K. Schneider 39-050

Cited by 1 publication

References 1 publication

Acetonitrile as a Building Block and Reactant

Acetonitrile as a Building Block and Reactant

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