Catalyst-Free Site Selective Hydroxyalkylation of 5-Phenylthiophen-2-amine with α-Trifluoromethyl Ketones through Electrophilic Aromatic Substitution

An original and effective approach for achieving trifluoromethyl hydroxyalkylation of 5-phenylthiophen-2-amine using α-trifluoromethyl ketones is described. In the last few years, reaction of Friedel-Crafts had been widely used to realize hydroxyalkylation on heterocycles such as indoles or thiophen...

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Published inMolecules (Basel, Switzerland) Vol. 27; no. 3; p. 925
Main Authors Duvauchelle, Valentin, Bénimélis, David, Meffre, Patrick, Benfodda, Zohra
Format Journal Article
LanguageEnglish
Published Switzerland MDPI AG 29.01.2022
MDPI
Subjects
Carbonyl compounds
Carbonyls
catalyst-free
Catalysts
Chemical Sciences
chemoselective
Communication
hydroxyalkylation
Imines
Indoles
Ketones
Lewis acid
Medicinal Chemistry
Organic chemistry
Reagents
site selective
Substitution reactions
Thiophenes
trifluoromethyl hydroxyalkylation
trifluoromethyl ketone
5-phenylthiophen-2-amine
trifluoromethyl hydroxyalkylation
hydroxyalkylation
catalyst-free
2-aminothiophene
chemoselective
site selective
trifluoromethyl ketone
trifluoromethyl hdroxyalkylation
Site selective
trifluoromethyl ketones
catalyst free
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Abstract An original and effective approach for achieving trifluoromethyl hydroxyalkylation of 5-phenylthiophen-2-amine using α-trifluoromethyl ketones is described. In the last few years, reaction of Friedel-Crafts had been widely used to realize hydroxyalkylation on heterocycles such as indoles or thiophenes by means of Lewis acid as catalyst. Additionally, amine functions are rarely free when carbonyl reagents are used because of their tendency to form imines. This is the first time that a site-selective electrophilic aromatic substitution on C atom of an unprotected 5-phenylthiophen-2-amine moiety is reported. The liberty to allow reaction in neutral conditions between free amine is valuable in a synthesis pathway. The reaction proceeds smoothly using an atom-economical metal-and catalyst-free methodology in good to excellent yields. A mechanism similar to an electrophilic aromatic substitution has been proposed.
AbstractList An original and effective approach for achieving trifluoromethyl hydroxyalkylation of 5-phenylthiophen-2-amine using α-trifluoromethyl ketones is described. In the last few years, reaction of Friedel-Crafts had been widely used to realize hydroxyalkylation on heterocycles such as indoles or thiophenes by means of Lewis acid as catalyst. Additionally, amine functions are rarely free when carbonyl reagents are used because of their tendency to form imines. This is the first time that a site-selective electrophilic aromatic substitution on C3 atom of an unprotected 5-phenylthiophen-2-amine moiety is reported. The liberty to allow reaction in neutral conditions between free amine is valuable in a synthesis pathway. The reaction proceeds smoothly using an atom-economical metal-and catalyst-free methodology in good to excellent yields. A mechanism similar to an electrophilic aromatic substitution has been proposed.
An original and effective approach for achieving trifluoromethyl hydroxyalkylation of 5-phenylthiophen-2-amine using α-trifluoromethyl ketones is described. In the last few years, reaction of Friedel-Crafts had been widely used to realize hydroxyalkylation on heterocycles such as indoles or thiophenes by means of Lewis acid as catalyst. Additionally, amine functions are rarely free when carbonyl reagents are used because of their tendency to form imines. This is the first time that a site-selective electrophilic aromatic substitution on C atom of an unprotected 5-phenylthiophen-2-amine moiety is reported. The liberty to allow reaction in neutral conditions between free amine is valuable in a synthesis pathway. The reaction proceeds smoothly using an atom-economical metal-and catalyst-free methodology in good to excellent yields. A mechanism similar to an electrophilic aromatic substitution has been proposed.
An original and effective approach for achieving trifluoromethyl hydroxyalkylation of 5-phenylthiophen-2-amine using α-trifluoromethyl ketones is described. In the last few years, reaction of Friedel-Crafts had been widely used to realize hydroxyalkylation on heterocycles such as indoles or thiophenes by means of Lewis acid as catalyst. Additionally, amine functions are rarely free when carbonyl reagents are used because of their tendency to form imines. This is the first time that a site-selective electrophilic aromatic substitution on C 3 atom of an unprotected 5-phenylthiophen-2-amine moiety is reported. The liberty to allow reaction in neutral conditions between free amine is valuable in a synthesis pathway. The reaction proceeds smoothly using an atom-economical metal-and catalyst-free methodology in good to excellent yields. A mechanism similar to an electrophilic aromatic substitution has been proposed.
Author Bénimélis, David
Benfodda, Zohra
Meffre, Patrick
Duvauchelle, Valentin
AuthorAffiliation UPR CHROME, Université de Nîmes, CEDEX 1, F-30021 Nîmes, France; valentin.duvauchelle@unimes.fr (V.D.); david.benimelis@unimes.fr (D.B.); patrick.meffre@unimes.fr (P.M.)
AuthorAffiliation_xml – name: UPR CHROME, Université de Nîmes, CEDEX 1, F-30021 Nîmes, France; valentin.duvauchelle@unimes.fr (V.D.); david.benimelis@unimes.fr (D.B.); patrick.meffre@unimes.fr (P.M.)
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crossref_primary_10_3390_molecules28155632
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Issue 3
Keywords 5-phenylthiophen-2-amine
trifluoromethyl hydroxyalkylation
hydroxyalkylation
catalyst-free
2-aminothiophene
chemoselective
site selective
trifluoromethyl ketone
trifluoromethyl hdroxyalkylation
Site selective
trifluoromethyl ketones
catalyst free
Language English
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Snippet An original and effective approach for achieving trifluoromethyl hydroxyalkylation of 5-phenylthiophen-2-amine using α-trifluoromethyl ketones is described. In...
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SourceType Open Website
Open Access Repository
Aggregation Database
Index Database
StartPage 925
SubjectTerms Carbonyl compounds
Carbonyls
catalyst-free
Catalysts
Chemical Sciences
chemoselective
Communication
hydroxyalkylation
Imines
Indoles
Ketones
Lewis acid
Medicinal Chemistry
Organic chemistry
Reagents
site selective
Substitution reactions
Thiophenes
trifluoromethyl hydroxyalkylation
trifluoromethyl ketone
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Title Catalyst-Free Site Selective Hydroxyalkylation of 5-Phenylthiophen-2-amine with α-Trifluoromethyl Ketones through Electrophilic Aromatic Substitution
URI https://www.ncbi.nlm.nih.gov/pubmed/35164190
https://www.proquest.com/docview/2627816654
https://search.proquest.com/docview/2629055375
https://hal.science/hal-03550954
https://pubmed.ncbi.nlm.nih.gov/PMC8839828
https://doaj.org/article/557fdeb22a554c99ad4755bc85fb3068
Volume 27
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