α-Fluorination of Nitrobenzenes and Nitropyridines via Vicarious Nucleophilic Substitution of Hydrogen

Synlett ◽

10.1055/s-0039-1690862 ◽

2020 ◽

Vol 31 (11) ◽

pp. 1094-1096

Author(s):

Michael F. Greaney ◽

Fayez Y. Al-Mkhaizim

Keyword(s):

Nucleophilic Substitution ◽

Reaction Times ◽

Nucleophilic Substitution Of Hydrogen ◽

Vicarious Nucleophilic Substitution ◽

Mild Conditions ◽

Electrophilic Fluorination

A highly selective C–H functionalization of nitrobenzenes and nitropyridines is reported using tandem vicarious nucleophilic substitution (VNS) chemistry with electrophilic fluorination using Selectfluor®. The process generates tertiary benzylic fluorides in good yield under simple, mild conditions and short reaction times.

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Reactions of organic anions, 147. Simple and general synthesis of hydroxy- and methoxyindoles via vicarious nucleophilic substitution of hydrogen

Liebigs Annalen der Chemie ◽

10.1002/jlac.198819880304 ◽

1988 ◽

Vol 1988 (3) ◽

pp. 203-208 ◽

Author(s):

Mieczysĺw Mąkosza ◽

Witold Danikiewicz ◽

Krzysztof Wojciechowski

Keyword(s):

Nucleophilic Substitution ◽

Organic Anions ◽

Nucleophilic Substitution Of Hydrogen ◽

Vicarious Nucleophilic Substitution ◽

General Synthesis

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A Simple and Efficient Synthesis of Alkyl (2-Nitroaryl)acetates and Alkyl 2-(2-Nitroaryl)propanoates via Vicarious Nucleophilic Substitution of Hydrogen in Nitroarenes by Carbanions or Alkyl Chloroacetates of Alkyl 2-Chloropropanoates

Synthesis ◽

10.1055/s-1988-27789 ◽

1988 ◽

Vol 1988 (12) ◽

pp. 1007-1009 ◽

Author(s):

B. Mudryk ◽

M. Mąkosza

Keyword(s):

Nucleophilic Substitution ◽

Nucleophilic Substitution Of Hydrogen ◽

Efficient Synthesis ◽

Vicarious Nucleophilic Substitution

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ChemInform Abstract: Reactions of Organic Anions. Part 194. Amination of Nitroarenes with Sulfenamides via Vicarious Nucleophilic Substitution of Hydrogen.

10.1002/chin.199305128 ◽

2010 ◽

Vol 24 (5) ◽

pp. no-no

Author(s):

M. MAKOSZA ◽

M. BIALECKI

Keyword(s):

Nucleophilic Substitution ◽

Organic Anions ◽

Nucleophilic Substitution Of Hydrogen ◽

Vicarious Nucleophilic Substitution

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ChemInform Abstract: 1,2,4-Triazines in Organic Synthesis. Part 17. Tandem Vicarious Nucleophilic Substitution of Hydrogen/Intramolecular Diels-Alder Reaction of 1,2,4-Triazines into Functionalized Cycloalkenopyridines.

10.1002/chin.200239149 ◽

2010 ◽

Vol 33 (39) ◽

pp. no-no

Author(s):

Danuta Branowska ◽

Stanislaw Ostrowski ◽

Andrzej Rykowski

Keyword(s):

Nucleophilic Substitution ◽

Organic Synthesis ◽

Alder Reaction ◽

Diels Alder ◽

Nucleophilic Substitution Of Hydrogen ◽

Vicarious Nucleophilic Substitution ◽

Diels Alder Reaction

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ChemInform Abstract: Asymmetric Aromatic Vicarious Nucleophilic Substitution of Hydrogen.

10.1002/chin.199723107 ◽

2010 ◽

Vol 28 (23) ◽

pp. no-no

Author(s):

M. D. DREW ◽

D. A. JACKSON ◽

N. J. LAWRENCE ◽

J. LIDDLE ◽

R. G. PRITCHARD

Keyword(s):

Nucleophilic Substitution ◽

Nucleophilic Substitution Of Hydrogen ◽

Vicarious Nucleophilic Substitution

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Reactions of Organic Anions, 177. Vicarious Nucleophilic Substitution of Hydrogen, Bisannulation and Competitive Reactions of α-Haloalkyl Carbanions with Bicyclic Azaaromatic Compounds

Chemische Berichte ◽

10.1002/cber.19911240325 ◽

1991 ◽

Vol 124 (3) ◽

pp. 577-585 ◽

Author(s):

Mieczyslaw Makosza ◽

Jerzy Golinski ◽

Stanislaw Ostrowski ◽

Arvind B. Sahasrabudhe ◽

Andrzej Rykowski

Keyword(s):

Nucleophilic Substitution ◽

Organic Anions ◽

Nucleophilic Substitution Of Hydrogen ◽

Vicarious Nucleophilic Substitution ◽

Competitive Reactions

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Vicarious nucleophilic substitution of hydrogen proceeding via heterocyclic ring opening

Tetrahedron ◽

10.1016/0040-4020(95)01104-8 ◽

1996 ◽

Vol 52 (9) ◽

pp. 3189-3194 ◽

Author(s):

Mieczyslaw Ma̧kosza ◽

Michal Sypniewski ◽

Tomasz Glinka

Keyword(s):

Nucleophilic Substitution ◽

Ring Opening ◽

Heterocyclic Ring ◽

Nucleophilic Substitution Of Hydrogen ◽

Vicarious Nucleophilic Substitution

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ChemInform Abstract: Chemistry of Ethanediyl S,S-Acetals. Part 6. An Example of Vicarious Nucleophilic Substitution of Hydrogen in 1,4-Benzodithians.

10.1002/chin.199412213 ◽

2010 ◽

Vol 25 (12) ◽

pp. no-no

Author(s):

R. CAPUTO ◽

M. DE NISCO ◽

G. PALUMBO ◽

C. ADAMO ◽

V. BARONE

Keyword(s):

Nucleophilic Substitution ◽

Nucleophilic Substitution Of Hydrogen ◽

Vicarious Nucleophilic Substitution

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ChemInform Abstract: Reactions of Organic Anions. Part 171. Direct Alkylation of Nitroarenes via Vicarious Nucleophilic Substitution of Hydrogen.

10.1002/chin.199127104 ◽

2010 ◽

Vol 22 (27) ◽

pp. no-no

Author(s):

Z. WROBEL ◽

M. MAKOSZA

Keyword(s):

Nucleophilic Substitution ◽

Organic Anions ◽

Nucleophilic Substitution Of Hydrogen ◽

Vicarious Nucleophilic Substitution

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Vicarious nucleophilic substitution of hydrogen versus vinylic substitution of halogen in the reactions of carbanions of halomethyl aryl sulfones with dialkyl halofumarates and halomaleates

Tetrahedron ◽

10.1016/s0040-4020(04)00610-6 ◽

2004 ◽

Author(s):

M MKOSZA

Keyword(s):

Nucleophilic Substitution ◽

Nucleophilic Substitution Of Hydrogen ◽

Vicarious Nucleophilic Substitution ◽

Vinylic Substitution

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