Reductive molybdenum‐catalyzed direct amination of boronic acids with nitro compounds

The synthesis of aromatic amines is of utmost importance in a wide range of chemical contexts. We report a direct amination of boronic acids with nitro compounds to yield (hetero)aryl amines. The novel combination of a dioxomolybdenum(VI) catalyst and triphenylphosphine as inexpensive reductant has...

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Detalles Bibliográficos
Autores: Suarez Pantiga, Samuel, Hernández Ruiz, Raquel, Virumbrales, Cintia, Pedrosa Sáez, María de los Remedios, Sanz Díez, Roberto
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2019
País:España
Institución:Universidad de Burgos (UBU)
Repositorio:Repositorio Institucional de la Universidad de Burgos (RIUBU)
OAI Identifier:oai:riubu.ubu.es:10259/5178
Acceso en línea:http://hdl.handle.net/10259/5178
Access Level:acceso abierto
Palabra clave:amination
boronic acids
molybdenum
nitro compounds
reduction
Química orgánica
Chemistry, Organic
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spelling Reductive molybdenum‐catalyzed direct amination of boronic acids with nitro compoundsSuarez Pantiga, SamuelHernández Ruiz, RaquelVirumbrales, CintiaPedrosa Sáez, María de los RemediosSanz Díez, Robertoaminationboronic acidsmolybdenumnitro compoundsreductionQuímica orgánicaChemistry, OrganicThe synthesis of aromatic amines is of utmost importance in a wide range of chemical contexts. We report a direct amination of boronic acids with nitro compounds to yield (hetero)aryl amines. The novel combination of a dioxomolybdenum(VI) catalyst and triphenylphosphine as inexpensive reductant has revealed to be decisive to achieve this new C-N coupling. Our methodology has proven to be scalable, air and moisture tolerant, highly chemoselective and engages both aliphatic and aromatic nitro compounds. More-over, this general and step-economical synthesis of aromatic secondary amines show cases orthogonality to other aromatic secondary amines show cases orthogonality to other aromatic amine syntheses as it tolerates aryl halides and carbonyl compounds.Junta de Castilla y León (BU022G18),Junta de Castilla y León and FEDER (BU076U16 and BU291P18) and Ministerio de Economía y Competitividad (MINECO) (CTQ2016-75023-C2-1-P)Wiley201920192019info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersionapplication/pdfhttp://hdl.handle.net/10259/5178reponame:Repositorio Institucional de la Universidad de Burgos (RIUBU)instname:Universidad de Burgos (UBU)EspañolAngewandte Chemie International Edition. 2019, V. 58, n. 11, p. 2129-2133https://doi.org/10.1002/anie.201812806info:eu-repo/grantAgreement/JCyL/U022G18/info:eu-repo/grantAgreement/JCyL/BU076U16/info:eu-repo/grantAgreement/JCyL/BU291P18/info:eu-repo/grantAgreement/MINECO/CTQ2016-75023-C2-1-P/info:eu-repo/semantics/openAccessoai:riubu.ubu.es:10259/51782026-05-28T07:56:11Z
dc.title.none.fl_str_mv Reductive molybdenum‐catalyzed direct amination of boronic acids with nitro compounds
title Reductive molybdenum‐catalyzed direct amination of boronic acids with nitro compounds
spellingShingle Reductive molybdenum‐catalyzed direct amination of boronic acids with nitro compounds
Suarez Pantiga, Samuel
amination
boronic acids
molybdenum
nitro compounds
reduction
Química orgánica
Chemistry, Organic
title_short Reductive molybdenum‐catalyzed direct amination of boronic acids with nitro compounds
title_full Reductive molybdenum‐catalyzed direct amination of boronic acids with nitro compounds
title_fullStr Reductive molybdenum‐catalyzed direct amination of boronic acids with nitro compounds
title_full_unstemmed Reductive molybdenum‐catalyzed direct amination of boronic acids with nitro compounds
title_sort Reductive molybdenum‐catalyzed direct amination of boronic acids with nitro compounds
dc.creator.none.fl_str_mv Suarez Pantiga, Samuel
Hernández Ruiz, Raquel
Virumbrales, Cintia
Pedrosa Sáez, María de los Remedios
Sanz Díez, Roberto
author Suarez Pantiga, Samuel
author_facet Suarez Pantiga, Samuel
Hernández Ruiz, Raquel
Virumbrales, Cintia
Pedrosa Sáez, María de los Remedios
Sanz Díez, Roberto
author_role author
author2 Hernández Ruiz, Raquel
Virumbrales, Cintia
Pedrosa Sáez, María de los Remedios
Sanz Díez, Roberto
author2_role author
author
author
author
dc.subject.none.fl_str_mv amination
boronic acids
molybdenum
nitro compounds
reduction
Química orgánica
Chemistry, Organic
topic amination
boronic acids
molybdenum
nitro compounds
reduction
Química orgánica
Chemistry, Organic
description The synthesis of aromatic amines is of utmost importance in a wide range of chemical contexts. We report a direct amination of boronic acids with nitro compounds to yield (hetero)aryl amines. The novel combination of a dioxomolybdenum(VI) catalyst and triphenylphosphine as inexpensive reductant has revealed to be decisive to achieve this new C-N coupling. Our methodology has proven to be scalable, air and moisture tolerant, highly chemoselective and engages both aliphatic and aromatic nitro compounds. More-over, this general and step-economical synthesis of aromatic secondary amines show cases orthogonality to other aromatic secondary amines show cases orthogonality to other aromatic amine syntheses as it tolerates aryl halides and carbonyl compounds.
publishDate 2019
dc.date.none.fl_str_mv 2019
2019
2019
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10259/5178
url http://hdl.handle.net/10259/5178
dc.language.none.fl_str_mv Español
language_invalid_str_mv Español
dc.relation.none.fl_str_mv Angewandte Chemie International Edition. 2019, V. 58, n. 11, p. 2129-2133
https://doi.org/10.1002/anie.201812806
info:eu-repo/grantAgreement/JCyL/U022G18/
info:eu-repo/grantAgreement/JCyL/BU076U16/
info:eu-repo/grantAgreement/JCyL/BU291P18/
info:eu-repo/grantAgreement/MINECO/CTQ2016-75023-C2-1-P/
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Wiley
publisher.none.fl_str_mv Wiley
dc.source.none.fl_str_mv reponame:Repositorio Institucional de la Universidad de Burgos (RIUBU)
instname:Universidad de Burgos (UBU)
instname_str Universidad de Burgos (UBU)
reponame_str Repositorio Institucional de la Universidad de Burgos (RIUBU)
collection Repositorio Institucional de la Universidad de Burgos (RIUBU)
repository.name.fl_str_mv
repository.mail.fl_str_mv
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