Cargando…

Fe(II)-catalysed insertion reaction of α-diazocarbonyls into X–H bonds (X = Si, S, N, and O) in dimethyl carbonate as a suitable solvent alternative

The insertion reaction of a broad range of diazo compounds into Si–H bonds was found to be efficiently catalysed by Fe(OTf)(2) in an emerging green solvent i.e. dimethyl carbonate (DMC). The α-silylated products were obtained in good to excellent yields (up to 95%). Kinetic studies showed that the e...

Descripción completa

Detalles Bibliográficos
Autores principales: Tanbouza, Nour, Keipour, Hoda, Ollevier, Thierry
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9073380/
https://www.ncbi.nlm.nih.gov/pubmed/35527937
http://dx.doi.org/10.1039/c9ra07203a
_version_ 1784701273063292928
author Tanbouza, Nour
Keipour, Hoda
Ollevier, Thierry
author_facet Tanbouza, Nour
Keipour, Hoda
Ollevier, Thierry
author_sort Tanbouza, Nour
collection PubMed
description The insertion reaction of a broad range of diazo compounds into Si–H bonds was found to be efficiently catalysed by Fe(OTf)(2) in an emerging green solvent i.e. dimethyl carbonate (DMC). The α-silylated products were obtained in good to excellent yields (up to 95%). Kinetic studies showed that the extrusion of N(2) to form an iron carbene intermediate is rate-limiting. The iron-catalysed insertion reaction of methyl α-phenyl-α-diazoacetate into polar X–H bonds (S–H, N–H, and O–H) was also established in DMC.
format Online
Article
Text
id pubmed-9073380
institution National Center for Biotechnology Information
language English
publishDate 2019
publisher The Royal Society of Chemistry
record_format MEDLINE/PubMed
spelling pubmed-90733802022-05-06 Fe(II)-catalysed insertion reaction of α-diazocarbonyls into X–H bonds (X = Si, S, N, and O) in dimethyl carbonate as a suitable solvent alternative Tanbouza, Nour Keipour, Hoda Ollevier, Thierry RSC Adv Chemistry The insertion reaction of a broad range of diazo compounds into Si–H bonds was found to be efficiently catalysed by Fe(OTf)(2) in an emerging green solvent i.e. dimethyl carbonate (DMC). The α-silylated products were obtained in good to excellent yields (up to 95%). Kinetic studies showed that the extrusion of N(2) to form an iron carbene intermediate is rate-limiting. The iron-catalysed insertion reaction of methyl α-phenyl-α-diazoacetate into polar X–H bonds (S–H, N–H, and O–H) was also established in DMC. The Royal Society of Chemistry 2019-10-02 /pmc/articles/PMC9073380/ /pubmed/35527937 http://dx.doi.org/10.1039/c9ra07203a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Tanbouza, Nour
Keipour, Hoda
Ollevier, Thierry
Fe(II)-catalysed insertion reaction of α-diazocarbonyls into X–H bonds (X = Si, S, N, and O) in dimethyl carbonate as a suitable solvent alternative
title Fe(II)-catalysed insertion reaction of α-diazocarbonyls into X–H bonds (X = Si, S, N, and O) in dimethyl carbonate as a suitable solvent alternative
title_full Fe(II)-catalysed insertion reaction of α-diazocarbonyls into X–H bonds (X = Si, S, N, and O) in dimethyl carbonate as a suitable solvent alternative
title_fullStr Fe(II)-catalysed insertion reaction of α-diazocarbonyls into X–H bonds (X = Si, S, N, and O) in dimethyl carbonate as a suitable solvent alternative
title_full_unstemmed Fe(II)-catalysed insertion reaction of α-diazocarbonyls into X–H bonds (X = Si, S, N, and O) in dimethyl carbonate as a suitable solvent alternative
title_short Fe(II)-catalysed insertion reaction of α-diazocarbonyls into X–H bonds (X = Si, S, N, and O) in dimethyl carbonate as a suitable solvent alternative
title_sort fe(ii)-catalysed insertion reaction of α-diazocarbonyls into x–h bonds (x = si, s, n, and o) in dimethyl carbonate as a suitable solvent alternative
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9073380/
https://www.ncbi.nlm.nih.gov/pubmed/35527937
http://dx.doi.org/10.1039/c9ra07203a
work_keys_str_mv AT tanbouzanour feiicatalysedinsertionreactionofadiazocarbonylsintoxhbondsxsisnandoindimethylcarbonateasasuitablesolventalternative
AT keipourhoda feiicatalysedinsertionreactionofadiazocarbonylsintoxhbondsxsisnandoindimethylcarbonateasasuitablesolventalternative
AT ollevierthierry feiicatalysedinsertionreactionofadiazocarbonylsintoxhbondsxsisnandoindimethylcarbonateasasuitablesolventalternative