Synthesis of substituted benzofurans by the tandem one-pot intramolecular carbolithiation-cyclization-substitution sequence

A convenient methodology for the synthesis of 3-sustituted-2,3- dihydrobenzofurans was developed based on the tandem intramolecular carbolithiation-cyclization of 2-bromophenyl-3-phenylprop-2-enyl ether, followed by trapping of the new lithiated intermediate by suitable electrophiles. Several electr...

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Autores principales: Rodríguez, C., Nudelman, N.S.
Formato: JOUR
Materias:
Alkylation
benzofurans
intramolecular carbocyclization
intramolecular carbolithiation
organolithium
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_00397911_v44_n6_p772_Rodriguez
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
id todo:paper_00397911_v44_n6_p772_Rodriguez
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spelling todo:paper_00397911_v44_n6_p772_Rodriguez2023-10-03T14:49:57Z Synthesis of substituted benzofurans by the tandem one-pot intramolecular carbolithiation-cyclization-substitution sequence Rodríguez, C. Nudelman, N.S. Alkylation benzofurans intramolecular carbocyclization intramolecular carbolithiation organolithium A convenient methodology for the synthesis of 3-sustituted-2,3- dihydrobenzofurans was developed based on the tandem intramolecular carbolithiation-cyclization of 2-bromophenyl-3-phenylprop-2-enyl ether, followed by trapping of the new lithiated intermediate by suitable electrophiles. Several electrophiles were tested, affording good to excellent yields. Alkyl bromides show better results than chlorides and when doubly halogenated alkyl chains are used as electrophiles only one position reacts, affording substituted benzofurans conveniently functionalized to undergo further reactions. The performance of both butyl and phenyllithium as lithiating agents was examined. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resource(s): Full experimental and spectral details.] © 2014 Taylor and Francis Group, LLC. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_00397911_v44_n6_p772_Rodriguez
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic Alkylation
benzofurans
intramolecular carbocyclization
intramolecular carbolithiation
organolithium
spellingShingle Alkylation
benzofurans
intramolecular carbocyclization
intramolecular carbolithiation
organolithium
Rodríguez, C.
Nudelman, N.S.
Synthesis of substituted benzofurans by the tandem one-pot intramolecular carbolithiation-cyclization-substitution sequence
topic_facet Alkylation
benzofurans
intramolecular carbocyclization
intramolecular carbolithiation
organolithium
description A convenient methodology for the synthesis of 3-sustituted-2,3- dihydrobenzofurans was developed based on the tandem intramolecular carbolithiation-cyclization of 2-bromophenyl-3-phenylprop-2-enyl ether, followed by trapping of the new lithiated intermediate by suitable electrophiles. Several electrophiles were tested, affording good to excellent yields. Alkyl bromides show better results than chlorides and when doubly halogenated alkyl chains are used as electrophiles only one position reacts, affording substituted benzofurans conveniently functionalized to undergo further reactions. The performance of both butyl and phenyllithium as lithiating agents was examined. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resource(s): Full experimental and spectral details.] © 2014 Taylor and Francis Group, LLC.
format JOUR
author Rodríguez, C.
Nudelman, N.S.
author_facet Rodríguez, C.
Nudelman, N.S.
author_sort Rodríguez, C.
title Synthesis of substituted benzofurans by the tandem one-pot intramolecular carbolithiation-cyclization-substitution sequence
title_short Synthesis of substituted benzofurans by the tandem one-pot intramolecular carbolithiation-cyclization-substitution sequence
title_full Synthesis of substituted benzofurans by the tandem one-pot intramolecular carbolithiation-cyclization-substitution sequence
title_fullStr Synthesis of substituted benzofurans by the tandem one-pot intramolecular carbolithiation-cyclization-substitution sequence
title_full_unstemmed Synthesis of substituted benzofurans by the tandem one-pot intramolecular carbolithiation-cyclization-substitution sequence
title_sort synthesis of substituted benzofurans by the tandem one-pot intramolecular carbolithiation-cyclization-substitution sequence
url http://hdl.handle.net/20.500.12110/paper_00397911_v44_n6_p772_Rodriguez
work_keys_str_mv AT rodriguezc synthesisofsubstitutedbenzofuransbythetandemonepotintramolecularcarbolithiationcyclizationsubstitutionsequence
AT nudelmanns synthesisofsubstitutedbenzofuransbythetandemonepotintramolecularcarbolithiationcyclizationsubstitutionsequence
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