Aerobic/Room-Temperature-Compatible s-Block Organometallic Chemistry in Neat Conditions: A Missing Synthetic Tool for the Selective Conversion of Nitriles into Asymmetric Alcohols

Highly-efficient and selective one-pot/two-step modular double addition of different highly polar organometallic reagents (RLi/RMgX) to nitriles en route to asymmetric tertiary alcohols (without the need for isolation/purification of any halfway reaction intermediate) has been studied, for the first...

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Autores: Elorriaga Muñoz, David, Parra Cadenas, Blanca, García Alvarez, Joaquín, Carrillo Hermosilla, Fernando, Antiñolo García, Antonio Fermín
Tipo de recurso: artículo
Fecha de publicación:2022
País:España
Institución:Universidad de Castilla-La Mancha
Repositorio:RUIdeRA. Repositorio Institucional de la UCLM
OAI Identifier:oai:ruidera.uclm.es:10578/41434
Acceso en línea:https://hdl.handle.net/10578/41434
Access Level:acceso abierto
Palabra clave:alcoholes asimétricos
nitrilos
Química inorgánica
Química organometálica
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spelling Aerobic/Room-Temperature-Compatible s-Block Organometallic Chemistry in Neat Conditions: A Missing Synthetic Tool for the Selective Conversion of Nitriles into Asymmetric AlcoholsElorriaga Muñoz, DavidParra Cadenas, BlancaGarcía Alvarez, JoaquínCarrillo Hermosilla, FernandoAntiñolo García, Antonio Fermínalcoholes asimétricosnitrilosQuímica inorgánicaQuímica organometálicaHighly-efficient and selective one-pot/two-step modular double addition of different highly polar organometallic reagents (RLi/RMgX) to nitriles en route to asymmetric tertiary alcohols (without the need for isolation/purification of any halfway reaction intermediate) has been studied, for the first time, in the absence of external/additional organic solvents (neat conditions), at room temperature and under air/moisture (no protecting atmosphere is required), which are generally forbidden reaction conditions in the field of highly-reactive organolithium/organomagnesium reagents. The one-pot modular tandem protocol demonstrated high chemoselectivity with a broad range of nitriles, as no side reactions (Li/halogen exchange, ortho-lithiations or benzylic metalations) were detected. Finally, this protocol could be scaled up, thus proving that this environmentally friendly methodology is amenable for a possible applied synthesis of asymmetric tertiary alcohols under bench type reaction conditions and in the absence of external organic solvents.Highly-efficient and selective one-pot/two-step modular double addition of different highly polar organometallic reagents (RLi/RMgX) to nitriles en route to asymmetric tertiary alcohols (without the need for isolation/purification of any halfway reaction intermediate) has been studied, for the first time, in the absence of external/additional organic solvents (neat conditions), at room temperature and under air/moisture (no protecting atmosphere is required), which are generally forbidden reaction conditions in the field of highly-reactive organolithium/organomagnesium reagents. The one-pot modular tandem protocol demonstrated high chemoselectivity with a broad range of nitriles, as no side reactions (Li/halogen exchange, ortho-lithiations or benzylic metalations) were detected. Finally, this protocol could be scaled up, thus proving that this environmentally friendly methodology is amenable for a possible applied synthesis of asymmetric tertiary alcohols under bench type reaction conditions and in the absence of external organic solvents.RSC202520252022info:eu-repo/semantics/articleapplication/pdfapplication/pdfhttps://hdl.handle.net/10578/41434reponame:RUIdeRA. Repositorio Institucional de la UCLMinstname:Universidad de Castilla-La ManchaInglésinfo:eu-repo/semantics/openAccessoai:ruidera.uclm.es:10578/414342026-05-27T07:36:41Z
dc.title.none.fl_str_mv Aerobic/Room-Temperature-Compatible s-Block Organometallic Chemistry in Neat Conditions: A Missing Synthetic Tool for the Selective Conversion of Nitriles into Asymmetric Alcohols
title Aerobic/Room-Temperature-Compatible s-Block Organometallic Chemistry in Neat Conditions: A Missing Synthetic Tool for the Selective Conversion of Nitriles into Asymmetric Alcohols
spellingShingle Aerobic/Room-Temperature-Compatible s-Block Organometallic Chemistry in Neat Conditions: A Missing Synthetic Tool for the Selective Conversion of Nitriles into Asymmetric Alcohols
Elorriaga Muñoz, David
alcoholes asimétricos
nitrilos
Química inorgánica
Química organometálica
title_short Aerobic/Room-Temperature-Compatible s-Block Organometallic Chemistry in Neat Conditions: A Missing Synthetic Tool for the Selective Conversion of Nitriles into Asymmetric Alcohols
title_full Aerobic/Room-Temperature-Compatible s-Block Organometallic Chemistry in Neat Conditions: A Missing Synthetic Tool for the Selective Conversion of Nitriles into Asymmetric Alcohols
title_fullStr Aerobic/Room-Temperature-Compatible s-Block Organometallic Chemistry in Neat Conditions: A Missing Synthetic Tool for the Selective Conversion of Nitriles into Asymmetric Alcohols
title_full_unstemmed Aerobic/Room-Temperature-Compatible s-Block Organometallic Chemistry in Neat Conditions: A Missing Synthetic Tool for the Selective Conversion of Nitriles into Asymmetric Alcohols
title_sort Aerobic/Room-Temperature-Compatible s-Block Organometallic Chemistry in Neat Conditions: A Missing Synthetic Tool for the Selective Conversion of Nitriles into Asymmetric Alcohols
dc.creator.none.fl_str_mv Elorriaga Muñoz, David
Parra Cadenas, Blanca
García Alvarez, Joaquín
Carrillo Hermosilla, Fernando
Antiñolo García, Antonio Fermín
author Elorriaga Muñoz, David
author_facet Elorriaga Muñoz, David
Parra Cadenas, Blanca
García Alvarez, Joaquín
Carrillo Hermosilla, Fernando
Antiñolo García, Antonio Fermín
author_role author
author2 Parra Cadenas, Blanca
García Alvarez, Joaquín
Carrillo Hermosilla, Fernando
Antiñolo García, Antonio Fermín
author2_role author
author
author
author
dc.subject.none.fl_str_mv alcoholes asimétricos
nitrilos
Química inorgánica
Química organometálica
topic alcoholes asimétricos
nitrilos
Química inorgánica
Química organometálica
description Highly-efficient and selective one-pot/two-step modular double addition of different highly polar organometallic reagents (RLi/RMgX) to nitriles en route to asymmetric tertiary alcohols (without the need for isolation/purification of any halfway reaction intermediate) has been studied, for the first time, in the absence of external/additional organic solvents (neat conditions), at room temperature and under air/moisture (no protecting atmosphere is required), which are generally forbidden reaction conditions in the field of highly-reactive organolithium/organomagnesium reagents. The one-pot modular tandem protocol demonstrated high chemoselectivity with a broad range of nitriles, as no side reactions (Li/halogen exchange, ortho-lithiations or benzylic metalations) were detected. Finally, this protocol could be scaled up, thus proving that this environmentally friendly methodology is amenable for a possible applied synthesis of asymmetric tertiary alcohols under bench type reaction conditions and in the absence of external organic solvents.
publishDate 2022
dc.date.none.fl_str_mv 2022
2025
2025
dc.type.none.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv https://hdl.handle.net/10578/41434
url https://hdl.handle.net/10578/41434
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv RSC
publisher.none.fl_str_mv RSC
dc.source.none.fl_str_mv reponame:RUIdeRA. Repositorio Institucional de la UCLM
instname:Universidad de Castilla-La Mancha
instname_str Universidad de Castilla-La Mancha
reponame_str RUIdeRA. Repositorio Institucional de la UCLM
collection RUIdeRA. Repositorio Institucional de la UCLM
repository.name.fl_str_mv
repository.mail.fl_str_mv
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