Reactions of lithiated aromatic heterocycles with carbon monoxide

The reaction of lithium derivatives of aromatic heterocycles with carbon monoxide was studied under several reaction conditions: 2-furyllithium afforded only one product, the tetrahydro-2-furaldehyde (25% yield). On the other hand, 2-thienyllithium and 5-methyl-2-furyllithium gave two and five produ...

Descripción completa

Detalles Bibliográficos
Autores principales: García Liñares, G.E., Nudelman, N.S.
Formato: JOUR
Materias:
Carbonylation
Electron transfer
Heterocycles
Mechanism
Organolithium
Radicals
Aromatic hydrocarbons
Carbon monoxide
Derivatives
Lithium
Reaction kinetics
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_08943230_v16_n8_p569_GarciaLinares
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
id todo:paper_08943230_v16_n8_p569_GarciaLinares
record_format dspace
spelling todo:paper_08943230_v16_n8_p569_GarciaLinares2023-10-03T15:41:59Z Reactions of lithiated aromatic heterocycles with carbon monoxide García Liñares, G.E. Nudelman, N.S. Carbonylation Electron transfer Heterocycles Mechanism Organolithium Radicals Aromatic hydrocarbons Carbon monoxide Carbonylation Derivatives Lithium Heterocycles Reaction kinetics The reaction of lithium derivatives of aromatic heterocycles with carbon monoxide was studied under several reaction conditions: 2-furyllithium afforded only one product, the tetrahydro-2-furaldehyde (25% yield). On the other hand, 2-thienyllithium and 5-methyl-2-furyllithium gave two and five products, respectively. Although in relatively low yields, formation of highly functionalized compounds takes place in a fast process under mild conditions. For 1,4-dihydroxy-1,4-bis(5-methyl-2-furanyl)butane-2,3-dione, reaction conditions were achieved to obtain this difficult to prepare derivative in 50% yield. To the best of our knowledge, this is the first report on the reaction of lithiated aromatic heterocycles with CO: evidence is given on the involvement of proton transfers in the reactions of 2-furyllithium and 2-thienyllithium, while the reaction of 5-methyl-2-furyllithium seems to proceed through an electron transfer as the first step. Copyright © 2003 John Wiley & Sons, Ltd. Fil:García Liñares, G.E. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_08943230_v16_n8_p569_GarciaLinares
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic Carbonylation
Electron transfer
Heterocycles
Mechanism
Organolithium
Radicals
Aromatic hydrocarbons
Carbon monoxide
Carbonylation
Derivatives
Lithium
Heterocycles
Reaction kinetics
spellingShingle Carbonylation
Electron transfer
Heterocycles
Mechanism
Organolithium
Radicals
Aromatic hydrocarbons
Carbon monoxide
Carbonylation
Derivatives
Lithium
Heterocycles
Reaction kinetics
García Liñares, G.E.
Nudelman, N.S.
Reactions of lithiated aromatic heterocycles with carbon monoxide
topic_facet Carbonylation
Electron transfer
Heterocycles
Mechanism
Organolithium
Radicals
Aromatic hydrocarbons
Carbon monoxide
Carbonylation
Derivatives
Lithium
Heterocycles
Reaction kinetics
description The reaction of lithium derivatives of aromatic heterocycles with carbon monoxide was studied under several reaction conditions: 2-furyllithium afforded only one product, the tetrahydro-2-furaldehyde (25% yield). On the other hand, 2-thienyllithium and 5-methyl-2-furyllithium gave two and five products, respectively. Although in relatively low yields, formation of highly functionalized compounds takes place in a fast process under mild conditions. For 1,4-dihydroxy-1,4-bis(5-methyl-2-furanyl)butane-2,3-dione, reaction conditions were achieved to obtain this difficult to prepare derivative in 50% yield. To the best of our knowledge, this is the first report on the reaction of lithiated aromatic heterocycles with CO: evidence is given on the involvement of proton transfers in the reactions of 2-furyllithium and 2-thienyllithium, while the reaction of 5-methyl-2-furyllithium seems to proceed through an electron transfer as the first step. Copyright © 2003 John Wiley & Sons, Ltd.
format JOUR
author García Liñares, G.E.
Nudelman, N.S.
author_facet García Liñares, G.E.
Nudelman, N.S.
author_sort García Liñares, G.E.
title Reactions of lithiated aromatic heterocycles with carbon monoxide
title_short Reactions of lithiated aromatic heterocycles with carbon monoxide
title_full Reactions of lithiated aromatic heterocycles with carbon monoxide
title_fullStr Reactions of lithiated aromatic heterocycles with carbon monoxide
title_full_unstemmed Reactions of lithiated aromatic heterocycles with carbon monoxide
title_sort reactions of lithiated aromatic heterocycles with carbon monoxide
url http://hdl.handle.net/20.500.12110/paper_08943230_v16_n8_p569_GarciaLinares
work_keys_str_mv AT garcialinaresge reactionsoflithiatedaromaticheterocycleswithcarbonmonoxide
AT nudelmanns reactionsoflithiatedaromaticheterocycleswithcarbonmonoxide
_version_ 1807321992069644288

Ejemplares similares