Synthesis of dithienoquinazolines from pyrimidines via intramolecular nucleophilic aromatic substitution of hydrogen
Sign Up to like & getrecommendations! Published in 2017 at "Chemistry of Heterocyclic Compounds"
DOI: 10.1007/s10593-017-2188-4
Abstract: The possibility of intramolecular nucleophilic aromatic substitution of hydrogen in the series of 5-[2-(het)aryl-1-benzothiophen-3-yl]-pyrimidines was explored. A convenient method for the synthesis of [1]benzothieno-[3,2-f]thieno[2,3-h]quinazoline and [1]benzothieno-[3,2-f]thieno[3,2-h]quinazoline based on the developed SNH protocol was proposed. The… read more here.
Keywords: nucleophilic aromatic; aromatic substitution; intramolecular nucleophilic; substitution hydrogen ... See more keywords
A Green Nucleophilic Aromatic Substitution Reaction
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DOI: 10.1021/acs.jchemed.0c00181
Abstract: This paper revisits the tie-dyeing process through a bioinspired and safer alternative to nucleophilic aromatic substitution (SNAr) reactions for an introductory organic chemistry laboratory. The s... read more here.
Keywords: substitution reaction; nucleophilic aromatic; chemistry; aromatic substitution ... See more keywords
Experimental Determination of Activation Energy of Nucleophilic Aromatic Substitution on Porphyrins
Sign Up to like & getrecommendations! Published in 2018 at "Journal of Chemical Education"
DOI: 10.1021/acs.jchemed.6b00940
Abstract: A physical organic chemistry experiment is described for second-year college students. Students performed nucleophilic aromatic substitution (NAS) reactions on 5,10,15,20-tetrakis(2,3,4,5,6-pentafluorophenyl)porphyrin (TPPF20) using three different nucleophiles. Substitution occurs preferentially at the 4-position (para) because it is… read more here.
Keywords: activation energy; nucleophilic aromatic; chemistry; aromatic substitution ... See more keywords
Palladium-Catalyzed Highly Regioselective Aromatic Substitution of Benzylic Ammonium Salts with Amines.
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DOI: 10.1021/acs.orglett.9b02820
Abstract: An unprecedented aromatic substitution reaction of benzylic ammonium salts has been developed through palladium-catalyzed C-N bond cleavage. A range of primary and secondary amines participated in a palladium-catalyzed aromatic substitution reaction of benzylic ammonium salts,… read more here.
Keywords: benzylic ammonium; aromatic substitution; ammonium salts; palladium catalyzed ... See more keywords
Non-Stabilized Vinyl Anion Equivalents from Styrenes by N-Heterocyclic Carbene Catalysis and Its Use in Catalytic Nucleophilic Aromatic Substitution.
Sign Up to like & getrecommendations! Published in 2022 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.2c02579
Abstract: A protocol for the catalytic nucleophilic activation of unactivated styrenes is reported, which enables the generation of a non-stabilized alkenyl anion equivalent as a transient intermediate. In the reaction, N-heterocyclic carbenes add across styrenes to… read more here.
Keywords: aromatic substitution; catalytic nucleophilic; non stabilized; nucleophilic aromatic ... See more keywords
Cation Radical Accelerated Nucleophilic Aromatic Substitution via Organic Photoredox Catalysis.
Sign Up to like & getrecommendations! Published in 2017 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.7b10076
Abstract: Nucleophilic aromatic substitution (SNAr) is a direct method for arene functionalization; however, it can be hampered by low reactivity of arene substrates and their availability. Herein we describe a cation radical-accelerated nucleophilic aromatic substitution using… read more here.
Keywords: radical accelerated; nucleophilic aromatic; accelerated nucleophilic; aromatic substitution ... See more keywords
Electrophilic Aromatic Substitution Reactions: Mechanistic Landscape, Electrostatic and Electric-Field Control of Reaction Rates, and Mechanistic Crossovers.
Sign Up to like & getrecommendations! Published in 2019 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.9b04982
Abstract: This study investigates the rich mechanistic landscape of the iconic electrophilic aromatic substitution (EAS) reaction class, in the gas phase, in solvents, and under stimulation by oriented external electric fields. The study uses DFT calculations,… read more here.
Keywords: reaction rates; control reaction; aromatic substitution; mechanistic landscape ... See more keywords
Electrophilic aromatic substitution over zeolites generates Wheland-type reaction intermediates
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DOI: 10.1038/s41929-017-0002-4
Abstract: AbstractThe synthesis of many industrial bulk and fine chemicals frequently involves electrophilic aromatic substitution (SEAr) reactions. The most widely practiced example of the SEAr mechanism is the zeolite-catalysed ethylation of benzene, using ethylene as an… read more here.
Keywords: wheland type; aromatic substitution; reaction; electrophilic aromatic ... See more keywords
Fast and accurate prediction of the regioselectivity of electrophilic aromatic substitution reactions† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c7sc04156j
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DOI: 10.1039/c7sc04156j
Abstract: A fast and user-friendly computational for predicting the regioselectivity of electrophilic aromatic substitution reactions of heteroaromatic systems is presented. read more here.
Keywords: aromatic substitution; electrophilic aromatic; regioselectivity electrophilic; substitution reactions ... See more keywords
σ-Holes promote the concertedness in nucleophilic aromatic substitution reactions of nitroarenes
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DOI: 10.1039/c9nj01493d
Abstract: Concertedness in SNAr may be modulated by the presence of a σ-hole. read more here.
Keywords: nucleophilic aromatic; promote concertedness; holes promote; aromatic substitution ... See more keywords
Nucleophilic aromatic substitution reactions under aqueous, mild conditions using polymeric additive HPMC
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DOI: 10.1039/d1gc00128k
Abstract: The use of the inexpensive, benign, and sustainable polymer, hydroxypropyl methylcellulose (HPMC), in water enables nucleophilic aromatic subsitution (SNAr) reactions between various nucleophiles and electrophiles. The mild reaction conditions facilitate a broad functional group tolerance… read more here.
Keywords: nucleophilic aromatic; mild conditions; aromatic substitution; aqueous mild ... See more keywords