Thiol anions in nucleophilic aromatic substitution reactions with activated aryl halides. Attack on carbon vs attack on halogen

1993 ◽  
Vol 58 (21) ◽  
pp. 5628-5631 ◽  
Author(s):  
Stefano Montanari ◽  
Cristina Paradisi ◽  
Gianfranco Scorrano
Keyword(s):  
Aryl Halides ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Substitution Reactions

Nucleophilic aromatic substitution reactions of unactivated aryl halides with thiolate ions in hexamethylphosphoramide

1979 ◽  
Vol 44 (15) ◽  
pp. 2642-2646 ◽  
Author(s):  
Pietro Cogolli ◽  
Filippo Maiolo ◽  
Lorenzo Testaferri ◽  
Marco Tingoli ◽  
Marcello Tiecco
Keyword(s):  
Aryl Halides ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Substitution Reactions

Microwave-assisted N-Arylation of Indoles via C(sp2)–N(sp2) Bond Formation by Aromatic Nucleophilic Substitution Reactions

2008 ◽  
Vol 63 (3) ◽  
pp. 298-302 ◽  
Author(s):  
Hui Xu ◽  
Ling-Ling Fan
Keyword(s):  
Reaction Time ◽  
Nucleophilic Substitution ◽  
Bond Formation ◽  
Aryl Halides ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Substitution Reactions ◽  
Aromatic Nucleophilic Substitution ◽  
Short Reaction Time ◽  
Microwave Assisted

Microwave-assisted nucleophilic aromatic substitution on aryl halides with different indoles is described. Moderate to good yields are obtained in short reaction time (25 - 40 min) when coupling indoles with fluoro- and chloro-substituted aryl halides under catalyst-free conditions.

scholarly journals Base-catalyzed aryl halide isomerization enables the 4-selective substitution of 3-bromopyridines

2020 ◽  
Vol 11 (38) ◽  
pp. 10517-10522
Author(s):  
Thomas R. Puleo ◽  
Jeffrey S. Bandar
Keyword(s):  
Aryl Halide ◽  
Aryl Halides ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Substitution Reactions ◽  
Selective Substitution

The base-catalyzed isomerization of aryl halides is described and applied to the tandem isomerization/4-substitution of 3-bromopyridines as a strategy for achieving unconventional selectivity in nucleophilic aromatic substitution reactions.

scholarly journals The use of bisphthalonitriles in the synthesis of side-strapped 1,11,15,25-tetrasubstituted phthalocyanines

1996 ◽  
Vol 74 (3) ◽  
pp. 307-318 ◽  
Author(s):  
Clifford C. Leznoff ◽  
David M. Drew
Keyword(s):  
Key Words ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Substitution Reactions ◽  
Pure Compounds

Nucleophilic aromatic substitution reactions of 3-nitrophthalonitrile yield 3-hydroxyphthalonitrile and 3-neopentoxyphthalonitrile, the latter of which condensed to 1,8,15,22-tetraneopentoxyphthalocyanine as a mixture of isomers. Bisphthalonitriles such as 1,3-bis(2′,3′-dicyanophenoxy)-2,2-dipentylpropane, 1,3-bis(2′,3′-dicyanophenoxy)-2,2-diethylpropane, 1,3-bis(2′,3′-dicyanophenoxy)-2,2-dioctylpropane, and 1,3-bis(2′,3′-dicyanophenoxy)-2-methyl-2-trityloxymethylpropane all gave bis-crown-like 1,11,15,25-tetrasubstituted phthalocyanines as pure compounds when treated with lithium octoxide in 1-octanol at 196 °C. A host of nine other bisphthalonitriles including 1,5-bis(2′,3′-dicyanophenoxy)-3-oxapentane, 1,1-bis(2′,3′-dicyanophenoxymethyl)cyclohexane, 1,2-bis(2′,3′-dicyanophenoxymethyl)benzene, and 2,5-bis(2′,3′-dicyanophenoxymethyl)furan did not dimerize to mononuclear phthalocynaines. The "gem dimethyl" effect was suggested as a reason for the successful macrocyclizations. Key words: nucleophilic aromatic substitution, phthalonitriles, bisphthalonitriles, 1,11,15,25-tetrasubstituted phthalocyanines.

scholarly journals Synthesis and fluorescent properties of N(9)-alkylated 2-amino-6-triazolylpurines and 7-deazapurines

2019 ◽  
Vol 15 ◽  
pp. 474-489 ◽  
Author(s):  
Andrejs Šišuļins ◽  
Jonas Bucevičius ◽  
Yu-Ting Tseng ◽  
Irina Novosjolova ◽  
Kaspars Traskovskis ◽  
...  
Keyword(s):  
Nucleophilic Aromatic Substitution ◽  
Secondary Amines ◽  
Acetonitrile Solution ◽  
Quantum Yields ◽  
Cell Labelling ◽  
Aromatic Substitution ◽  
Fluorescent Properties ◽  
Substitution Reactions ◽  
Low Cytotoxicity ◽  
Electron Donating Groups

The synthesis of novel fluorescent N(9)-alkylated 2-amino-6-triazolylpurine and 7-deazapurine derivatives is described. A new C(2)-regioselectivity in the nucleophilic aromatic substitution reactions of 9-alkylated-2,6-diazidopurines and 7-deazapurines with secondary amines has been disclosed. The obtained intermediates, 9-alkylated-2-amino-6-azido-(7-deaza)purines, were transformed into the title compounds by CuAAC reaction. The designed compounds belong to the push–pull systems and possess promising fluorescence properties with quantum yields in the range from 28% to 60% in acetonitrile solution. Due to electron-withdrawing properties of purine and 7-deazapurine heterocycles, which were additionally extended by triazole moieties, the compounds with electron-donating groups showed intramolecular charge transfer character (ICT/TICT) of the excited states which was proved by solvatochromic dynamics and supported by DFT calculations. In the 7-deazapurine series this led to increased fluorescence quantum yield (74%) in THF solution. The compounds exhibit low cytotoxicity and as such are useful for the cell labelling studies in the future.

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